Heterocyclic Building Blocks-Isoquinoline

630421-73-7,630421-73-7, 1,6-Dichloroisoquinoline is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

1,6-dichloroisoquinoline (4.80 g, 24.2 mmol), 2,6-dimethyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuro[2,3-b]pyridine (8.22 g, 25.4 mmol), sodium carbonate (6.42 g, 60.6 mmol), palladium tetrakis (0.84 g, 0.73 mmol), 160 mL dimethoxyethane (DME) and 40 mL of water were combined in a round bottom flask. A condenser was attached and then the system was evacuated and purged with nitrogen three times. The reaction mixture was heated to a vigorous reflux overnight. The reaction mixture was diluted with ethyl acetate and water, the suspension was then filtered through Celite and washed with ethyl acetate. The aqueous portion was partitioned off and the organic was washed once with brine, dried with sodium sulfate, filtered, and concentrated down to beige solid. The Celite was further washed with 50/50 DCM/THF and the filtrate was concentrated and combined with the other crude sample. The combined crude sample was dissolved in DCM and purified with silica gel using DCM to 85/15 DCM/ethyl acetate solvent system to get a pale beige solid. The pale beige solid was triturated in 90/10 heptane/ethyl acetate, then filtered to get a white precipitate of 8-(6-chloroisoquinolin-1-yl)-2,6-dimethylbenzofuro[2,3-b]pyridine (7.8 g, 91% yield).

630421-73-7 1,6-Dichloroisoquinoline 23595199, aisoquinoline compound, is more and more widely used in various.

Reference£º
Patent; Universal Display Corporation; Boudreault, Pierre-Luc T.; Adamovich, Vadim; Yamamoto, Hitoshi; Wendt, Harvey; Xia, Chuanjun; EP2940098; (2015); A1;,
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Isoquinoline | C9H7N – PubChem

893566-75-1, Tert-butyl 8-bromo-3,4-dihydroisoquinoline-2(1H)-carboxylate is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,893566-75-1

A mixture of tert-butyl 8-bromo-3,4-dihydroiso- quinoline-2(1H)-carboxylate (500 mg, 1.60 mmol), Nal (720 mg, 4.80 mmol), Cul (45.8 mg, 0.240 mmol) and trans-N,Ndimethylcyclohexanediamine (68 mg, 0.48 mmol) in dioxane (10 mE) was purged with N2 for 10 mm. The resulting yellow suspension was stirred at 110¡ã C. in a sealed tube for 20 hrs. ECMS showed 50percent conversion, therefore additional Nal (720 mg, 4.80 mmol), Cul (45.8 mg, 0.24 mmol) and trans-N,N-dimethylcyclohexanediamine (68 mg, 0.40 mmol) was added followed by N2 purging for 10 mm. The resulting yellow suspension was stirred at 110¡ã C. in a sealed tube for 20 hrs. The mixture was poured into water (20 mE) and extracted with EtOAc (10 mEx3). The extract was concentrated in vacuo to afford crude material which was purified by silica gel chromatography eluted with EtOAc in petroleum ether from 0 to 20percent to afford the product (450 mg, 78percent) as a light yellow oil. ECMS [M-tBu]304; 1H NMR (400 MHz, CDCl3) oe ppm 7.70 (d, J=8.0 Hz, 1H), 7.12 (d, J=7.0 Hz, 1H), 6.94-6.82 (m, 1H), 4.44 (m, 2H), 3.62 (t, J=5.5 Hz, 2H), 2.81 (br. s., 2H), 1.50 (s, 9H)

The synthetic route of 893566-75-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Pfizer Inc.; Tatlock, John Howard; McAlpine, Indrawan James; Tran-Dube, Michelle Bich; Rui, Eugene Yuanjin; Wythes, Martin James; Kumpf, Robert Arnold; McTigue, Michele Ann; (181 pag.)US2016/244475; (2016); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.18881-17-9,(S)-(1,2,3,4-Tetrahydroisoquinolin-3-yl)methanol,as a common compound, the synthetic route is as follows.,18881-17-9

(35)-l,2,3,4-tetrahydroisoquinolin-3-ylmethanol (82.0 mg, 0.50 mmol) was added to a stirred solution of (3ai?,7ai?)-hexahydro-2-benzofuran-l,3-dione (77.0 mg, 0.50 mmol) and DIPEA (0.88 uL, 0.50 mmol) in DCM (2.5 mL). The reaction was stirred overnight and then concentrated in vacuo. To the residue was added fresh THF (2.5 mL) followed by l-aminocyclopropanecarbonitrile hydrochloride (65.0 mg 0.55 mmol), DMTMM (153 mg 0.55 mmol) and DIPEA (88 uL, 0.50 mmol) was added and the reaction stirred for 4 nights, poured into water (30 mL) and extracted with ethyl acetate (2 x 25 mL), the organics were washed with sat. sodium carbonate solution (25 mL), water (25 mL), IM HCl (25 mL), water (25 mL) and then brine (25 mL), dried over MgSO4, filtered and concentrated in vacuo. Purified on the basic preparative HPLC (NH4OH modifier).LCMS retention time 1.75 min. (+ve ESI) : 382 (M+H)+

The synthetic route of 18881-17-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/1128; (2008); A1;,
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Isoquinoline | C9H7N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1350643-72-9,(S)-3-(1-Aminoethyl)-8-chloro-2-phenylisoquinolin-1(2H)-one,as a common compound, the synthetic route is as follows.

[401] To a suspension of (5)-3-(l-aminoethyl)-8-chloro-2-phenylisoquinolin-l(2H)-one (51.3 mg, 0.172 mmol), 6-chloro-5-(3-ethyl-l,2,4-oxadiazol-5-yl)pyrimidin-4-amine (46.3 mg, 0.205 mmol) and DIPEA (29.9 mg, 0.231mmol) in propan-l-ol (2.0 mL), and then the mixture was heated at 100 C with stirring for 5 hours. The mixture was concentrated in vacuo and the residue was purified by a silica gel column chromatography (DCM/MeOH (v/v) = 100/1) to give the title compound as a pale yellow solid (54 mg, 65%). MS (ESI, pos. ion) m/z: 487.8 [M+H]+; NMR (400 MHz, CDCb) delta (ppm): 8.32 (d, J= 5.8 Hz, 1H), 8.02 (s, 1H), 7.55-7.39 (m, 6H), 7.33 (t, J = 8.4 Hz, 2H), 6.51 (s, 1H), 5.10-4.83 (m, 1H), 2.85 (q, J = 7.5 Hz, 2H), 1.44 (d, J = 6.7 Hz, 3H), 1.38 (t, J= 7.5 Hz, 3H)., 1350643-72-9

1350643-72-9 (S)-3-(1-Aminoethyl)-8-chloro-2-phenylisoquinolin-1(2H)-one 66607319, aisoquinoline compound, is more and more widely used in various.

Reference£º
Patent; SUNSHINE LAKE PHARMA CO., LTD.; CALITOR SCIENCES, LLC; XI, Ning; WANG, Tingjin; FENG, Xuejin; WU, Shuang; ZHANG, Tao; WANG, Liang; (139 pag.)WO2016/149160; (2016); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.105627-79-0,Isoquinoline-5-sulfonyl chloride hydrochloride,as a common compound, the synthetic route is as follows.

EXAMPLE 1 52.8 g of 5-isoquinolinesulfonyl chloride hydrochloride was dissolved in 200 ml of water and extracted with 300 ml of dichloromethane. The resultant aqueous layer was taken out and adjusted to pH 5 with a saturated aqueous sodium hydrogencarbonate solution, and subjected to extraction with 200 ml dichloromethane. Then, the dichloromethane layers were mixed together and added dropwise to a dichloromethane solution (300 ml) containing 24.4 g of ethanolamine over 30 minutes while cooling with ice. The precipitated crystal was subjected to filtration, washed successively with 300 ml of water and 200 ml of ethyl acetate, and dried under reduced pressure at 40 C., to thereby obtain 40.0 g of N-(2-hydroxyethyl)-5-isoquinolinesulfonamide (yield: 79%).

105627-79-0, As the paragraph descriping shows that 105627-79-0 is playing an increasingly important role.

Reference£º
Patent; Asahi Kasei Kogyo Kabushiki Kaisha; US5340811; (1994); A;,
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Isoquinoline | C9H7N – PubChem

93117-08-9,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.93117-08-9,5-Aminoisoquinolin-1(2H)-one,as a common compound, the synthetic route is as follows.

The triazolinium compound (9b) was synthesized as described in Scheme 2: 5-amino-isoquinolinone (50 mg, 1 eq, 0.312 mmol) was dissolved in 50% / 50% solution of water/hydrochloric acid (2.5 mL / 2.5 mL) in the dark. The mixture was cooled to -5 C. A solution of sodium nitrite (43.1 mg, 2 eq, 0.624 mmol) in water (1 mL) was added dropwise. After 15 min at -5 C, a solution of bis(2-chloroethyl)amine hydrochloride (334 mg, 6 eq, 1.87 mmol) in water (2 mL) was added slowly dropwise directly. After 30 min at -5 C, the mixture was added dropwise to a saturated solution of sodium bicarbonate and left to precipitate for an hour. Filtration of the mixture yielded a dark-brown solid (10 mg, 10%). 1H NMR (300 MHz, DMSO-d6) delta 11.72 (s, 1H, NH), 8.38 (d, 1H, J = 8.1 Hz, ArH), 8.00 (dd, 1H, J = 7.8 Hz, 1.2 Hz, ArH), 7.67 (t, 1H, J = 7.8 Hz, ArH), 7.37 (t, 1H, J = 6.6 Hz, ArH), 6.77 (d, 1H, J = 7.5 Hz, ArH), 4.92 (t, 2H, J = 13.2 Hz, N+CH2CH2N), 4.69 (t, 2H, J = 12.9 Hz, NCH2CH2N+), 4.56 (t, 2H, J = 5.4 Hz, ClCH2CH2N), 4.15 (t, 2H, J = 5.1 Hz, NCH2CH2Cl). 13C NMR (400 MHz, DMSO-d6): delta ppm 161.29, 132.64, 132.12, 131.79, 129.74, 128.40, 128.15, 126.80, 99.18, 55.96, 54.94, 54.79 and 40.82. ESI m/z 311 (M-).

The synthetic route of 93117-08-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Goodfellow, Elliot; Senhaji Mouhri, Zhor; Williams, Christopher; Jean-Claude, Bertrand J.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 3; (2017); p. 688 – 694;,
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164148-92-9, tert-Butyl 6-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step-2: Synthesis of tert-butyl 7-((1-(2-(tert-butyl)pyridin-4-yl)-2-cyclopropyl-3-oxo-2,3-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)amino)-3,4-dihydroisoquinoline-2(1H)-carboxylate To a stirred solution of 1-(2-(tert-butyl)pyridin-4-yl)-2-cyclopropyl-6-(methylthio)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one (196 mg, 0.548 mmol, 1.0 eq) in (6.0 mL) of toluene was added m-CPBA (189 mg, 1.096 mmol, 2.0 eq) and allowed to stir at rt for 1 h. tert-butyl 6-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate (163 mg, 0.657 mmol, 1.2 eq) and DIPEA (0.37 mL, 2.192 mmol, 4.0 eq) were added and allowed to stir at rt for overnight. After completion of reaction, the reaction mixture was diluted with water and extracted with EtOAc (50 mL*2). The combined organic layer was washed with water (50 mL), brine solution (50 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford crude product, which was purified by flash chromatography [silica gel 100-200 mesh; elution 0-50% EtOAc in hexane] to afford the desired compound, tert-butyl 7-((1-(2-(tert-butyl)pyridin-4-yl)-2-cyclopropyl-3-oxo-2,3-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)amino)-3,4-dihydroisoquinoline-2(1H)-carboxylate (100 mg, 32.63%) as an off white solid.

164148-92-9, The synthetic route of 164148-92-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; giraFpharma LLC; Chakravarty, Sarvajit; PHAM, Son Minh; Kankanala, Jayakanth; AGARWAL, Anil Kumar; PUJALA, Brahmam; SONI, Sanjeev; ARYA, Satish K.; PALVE, Deepak; Gupta, Ashu; KUMAR, Varun; (498 pag.)US2019/106427; (2019); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.22960-16-3,Isoquinoline-4-carbaldehyde,as a common compound, the synthetic route is as follows.

22960-16-3, Step A 4-Hydroxymethylisoquinoline 4-Isoquinolinecarboxaldehyde (6.15 g, 39.13 mmoles) (prepared by the method of: J. B. Wommack. T. G. Barbee, Jr., D. J. Thoennes, M. A. McDonald and D. E. Pearson, J. Heterocyclic Chem., 1969, 6, 243-245.) was dissolved in anhydrous dichloromethane (369 mL) and the solution was cooled to 0 C. Borane-dimethyl sulfide complex (1 M in THF) (5.23 mL, 5.09 mmoles) (as described in: E. Mincione, J. Org. Chem., 1978, 43, 1829-1830) was added and the mixture was stirred at 0 C. for a 1.5 h. Additional borane-dimethylsulfide complex (1 M in THF) (10.455 mL, 1.35 mmoles) was added and the reaction was stirred for an additional 2 h at 0 C. Methanol (93.3 mL) was added and the solution was evaporated to dryness and chromatographed on silica gel using 2-3% (10% conc. NH4OH in methanol)-dichloromethane as the eluant to give unreacted 4-Isoquinolinecarboxaldehyde (~23%), 4(1.2-dihydroisoquinoline)carboxaldehyde (identical to that described in Preparative Example 63.

The synthetic route of 22960-16-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Schering Corporation; US6362188; (2002); B1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

105627-79-0, Isoquinoline-5-sulfonyl chloride hydrochloride is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a suspension of isoquinoline-5-sulphonic acid (237 mg, 1.133 mmol) in thionyl chloride (1.1 ml) was added DMF (20 U, L) and the mixture refluxed for 3 h. The resulting precipitate was cooled, concentrated and used as the crude hydrochloride salt. To a solution of the hydrochloride salt of the Boc-protected pyrrolidine derivative shown above (265 mg, 0.944 mmol) in DCM (9 ml) at rt was added triethylamine (658 PI, 4.720 mmol) and DMAP (20 mg, 0.164 mmol). The crude sulphonyl chloride prepared above was added in one portion and the resulting mixture stirred for 1 h. Brine (20 ml) was added, the phases separated and the aqueous further extracted with DCM (3 x 15 ml). Organic phases were combined, dried (MGSO4), concentrated and the crude purified by silica column chromatography (5% MeOH/DCM) to give the desired product as an oil (309 mg, 63%). 1H NMR (CDC13) 8 1.27 (9H, s), 1.81-2. 24 (2H, m), 2.90-3. 12 (1H, m), 3.37-3. 50 (1H, M), 3.62 (3H, s), 3.77-3. 94 (1H, m), 4.10-4. 27 (1H, m), 5.91-6. 27 (1H, m), 7.60-7. 68 (1H, m), 8.15-8. 18 (1H, m), 8.31-8. 41 (2H, m), 8.55-8. 62 (1H, m), 9.30 (1H, s).

105627-79-0, 105627-79-0 Isoquinoline-5-sulfonyl chloride hydrochloride 13116932, aisoquinoline compound, is more and more widely used in various.

Reference£º
Patent; ASTEX TECHNOLOGY LIMITED; CANCER RESEARCH TECHNOLOGY LIMITED; THE INSTITUTE OF CANCER RESEARCH: ROYAL CANCER HOSPITAL; WO2005/11697; (2005); A2;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.20232-39-7,6,7-Dimethoxy-3,4-dihydroisoquinoline hydrochloride,as a common compound, the synthetic route is as follows.

General procedure: In a 10 mL pressurized reaction vial, 0.5 mmolindole (1) or indole-2-carboxylic acid (6), 0.5mmol cyclic imine (2, 4, 9or 12) and Et3N (for theamount used see Table 1) were placed. Thereaction mixture was heated in an oil bath or in a CEM Discover SP MW reactor.The reaction conditions are listed in Tables 1 and 2 and the work-up procedurein the text

20232-39-7, As the paragraph descriping shows that 20232-39-7 is playing an increasingly important role.

Reference£º
Article; Szatma?ri, Istva?n; Sas, Judit; Fu?lo?p, Ferenc; Tetrahedron Letters; vol. 54; 37; (2013); p. 5069 – 5071;,
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Isoquinoline | C9H7N – PubChem