Category: isoquinoline

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.6624-49-3,Isoquinoline-3-carboxylic acid,as a common compound, the synthetic route is as follows.

6624-49-3, Isoquinoline-3-carboxylic acid (500 mg, 2.89 mmol), glycine methyl ester hydrochloride (363 mg, 2.89 mmol, 1 eq), PyBOP (1.65 g, 3.18 mmol, 1.2 eq) and Et3N (400 mu, 2.89 mmol, 1 eq) were dissolved in the anhydrous DMF (10 mL) and stirred at room temperature for 24h. Upon completion of the reaction the DMF was evaporated in vacuo and the resultant residue was suspended in CH2CI2 (20 mL) and washed with H20 (2 x 10 mL). The organic phase was dried over MgS04, filtered and subjected to the column chromatography (eluent system: cHex/EtOAc). The obtained product was dissolved in a mixture of THF/H20 (1 : 1, 10 mL) and treated with LiOH H20 (600 mg, 14.45 mmol, 5 eq). The reaction was stirred at room temperature for 12h. The TFIF was evaporated in vacuo and the remaining aqueous solution was neutralized with cone. HCl. The precipitate was collected by filtration and dried in vacuo to yield the desired product (266 mg, 1.16 mmol, 40percent). 1H NMR (400 MHz, DMSO-i) delta = 9.42 (s, 1 H, H6), 9.14 (t, J=6.0 Hz, 1 H, H), 8.58 (si H, H5), 8.27 (d, J=8.0 Hz, 1 H, H3), 8.22 (d, J=8.0 Hz, 1 H, H4) 7.90 (ddd, J=8.0, 7.0, 1.0 Hz, 1 H, H2) 7.83 (ddd, J=8.0, 7.0, 1.0 Hz, 1 H, HI) 4.05 (d, J=6.0 Hz, 2 H, H7 , H7//)ppm. 13C NMR (101 MHz, DMSO-i) delta = 171.7, 164.9, 152.1, 143.8, 135.8, 131.9, 129.8, 129.7, 128.5, 128.3, 120.3, 41.6 ppm. Mp = 208-210 ¡ãC (223-224 ¡ãC)21. HRMS (ESI-TOF) calcd for Ci2Hi0N2NaO3 [M+Na+] : 253.0584, found: 253.0595, FT-IR vmax (neat): 3378, 1733, 1631, 1531, 1233, 766 cm”1.

The synthetic route of 6624-49-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ISIS INNOVATION LIMITED; SCHOFIELD, Christopher Joseph; RYDZIK, Anna; MCDONOUGH, Michael; CHOWDHURY, Rasheduzzaman; WO2015/92412; (2015); A1;,
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1041423-28-2, 3-Chloro-6-fluoroisoquinoline is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 4: 16.5 g of (cis-4-hydroxy-cyclohexyl)-carbamic acid tert-butyl ester were dissolved in 210 ml of diglyme and treated with 4.1g 50% NaH under nitrogen. The resulting mixture was stirred for 1 h at room temperature, then 14.8 g of the product from Step 3 were added. The mixture was allowed to stir for 1 day at room temperature, then 100 ml of toluene were added and the resulting mixture was washed with water 3 times. The organic phases were collected and the solvent was removed in vacuo., 1041423-28-2

As the paragraph descriping shows that 1041423-28-2 is playing an increasingly important role.

Reference£º
Patent; SANOFI-AVENTIS; WO2008/77554; (2008); A1;,
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147497-32-3, 6-Bromo-3,4-dihydroisoquinolin-1(2H)-one is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 1 Preparation of 6-bromo-1,2,3,4-tetrahydroisoquinoline A solution of 6-bromo-3,4-dihydro-1(1H)-isoquinolinone (Example 31, Step 1; 5.5 g, 1.0 mmol) in THF (25 mL) was treated with 1M BH3 in THF (5 mL, 5 mmol) and heated at reflux for 20 h. To the mixture was added MeOH (5 mL), the solvent removed and the residue heated with 2N HCl for 3 h. The reaction was cooled, made basic with aqueous NH4 OH and extracted with CH2 Cl2, dried and evaporated to give the title compound as a gum which was used as such., 147497-32-3

The synthetic route of 147497-32-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Merck & Co., Inc.; US5977134; (1999); A;,
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347146-33-2, 1-Chloroisoquinolin-6-amine is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

SYNTHETIC EXAMPLE 61b 1-Chloro-6-(4-cyanobenzenesulfonylamino)isoquinoline The title compound was obtained using 6-amino-1-chloro-isoquinoline (Production Example 23b) and 4-cyanobenzenesulfonyl chloride in the same method as in Synthetic Example 1b. 1H-NMR(DMSO-d6) delta (ppm): 7.52(1H, dd, J=2.0, 8.8 Hz), 7.68(1H, d, J=2.0 Hz), 7.79(1H, d, J=5.6 Hz), 8.03(4H, m), 8.18(1H, d, J=5.6 Hz), 8.21(1H, d, J=8.8 Hz), 11.36(1H, s)., 347146-33-2

347146-33-2 1-Chloroisoquinolin-6-amine 22674114, aisoquinoline compound, is more and more widely used in various fields.

Reference£º
Patent; Wakabayashi, Toshiaki; Funahashi, Yasuhiro; Hata, Naoko; Semba, Taro; Yamamoto, Yuji; Haneda, Toru; Owa, Takashi; Tsuruoka, Akihiko; Kamata, Junichi; Okabe, Tadashi; Takahashi, Keiko; Nara, Kazumasa; Hamaoka, Shinichi; Ueda, Norihiro; US2004/18192; (2004); 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.1196-38-9,3,4-Dihydroisoquinolin-1(2H)-one,as a common compound, the synthetic route is as follows.

Sodium Hydride (31 .8 mg, 0.796 mmol) was added to DMF (1 mL), followed by 3,4-dihydro-1 (2H)- isoquinolinone (107 mg, 0.730 mmol). The resulting suspension was stirred at r.t. for 5 min, then 4,6- dichloro-2-(2-pyridinyl)pyrimidine (150 mg, 0.664 mmol) was added and resulting mixture was stirred at r.t. for 45 min.The mixture was partitioned between EtOAc and water then the aqueous layer extracted with DCM three times. The organic layers were combined, filtered throught a phase separator and volatiles removed under reduced pressure to afford 212 mg of a white-brown powder.The crude material was purified by column chromatography, eluting with a 0 to 100percent EtOAc in cyclohexane, to give the title compound, 121 mg (54percent) as an off white powder.LCMS (Method A) Rt 1 .05 min, MH+=337.0, 1196-38-9

The synthetic route of 1196-38-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; GLAXO GROUP LIMITED; ATKINSON, Stephen John; BARKER, Michael David; CAMPBELL, Matthew; HUMPHREYS, Philip; LIDDLE, John; SHEPPARD, Robert John; WILSON, David; WO2012/52390; (2012); A1;,
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7159-36-6, Isoquinoline-4-carboxylic acid is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,7159-36-6

EXAMPLE 51; l-rdsoquinoline-^carbonvD-aminol-indan-l-carboxylic acid ethyl ester (51):To a solution of isoquinoline-4-carboxylic acid (21 lmg, 1.22mmol), 2-amino-indan-2- carboxylic acid ethyl ester (250mg, 1.22mmol), HATU (696mg, 1.83mmol) in anhydrous DMF (8mL) is added DIPEA (302muL, 1.83mmol). The resulting solution is stirred at RT overnight. After the removal of DMF in vacuo, the residue is dissolved in EtOAc (4OmL) and washed with water (I x 1OmL) and brine (2 x 1OmL). The organic layer is dried over anhydrous Na2SO4 and concentrated in vacuo. The residue is purified by flash column chromatography (115g silica gel, gradient elution: 5-50percent EtOAc in heptane) to give a pure product (51) as white solid (359mg, 82percent).74 1H NMR (CDCl3, 300MHz): delta 1.26(t, 3H), 3.49 (d, 2H), 3.79(d, 2H), 4.28(q, 2H), 6.96(s, IH), 7.20-7.27(m, 4H), 7.57-7.62(m, IH), 7.76-7.82(m, IH), 7.86(d, IH), 8.12(d, IH), 8.54(d, IH), 9.22(d, IH) LC/MS (ES+) m/z = 361.15

As the paragraph descriping shows that 7159-36-6 is playing an increasingly important role.

Reference£º
Patent; SANOFI-AVENTIS; WO2008/151211; (2008); A1;,
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1350643-72-9, (S)-3-(1-Aminoethyl)-8-chloro-2-phenylisoquinolin-1(2H)-one is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of 2-cyanoacetyl chloride (5.1 mmol, 1.0 eq) in DCM (10 mL) at 0 C., Compound 1 (1.0 eq) and triethylamine (1.5 eq) were added. The resulting mixture was warmed to RT and stirred for 2 h. The mixture was partitioned between DCM and a saturated aqueous sodium bicarbonate solution. The organic phase was separated, dried with sodium sulfate, pre-adsorbed on silica gel and purified on silica gel column with acetone and DCM to afford nitrile 136. ESI-MS m/z: 366.3 [M+H]+., 1350643-72-9

As the paragraph descriping shows that 1350643-72-9 is playing an increasingly important role.

Reference£º
Patent; Intellikine LLC; Infinity Pharmaceuticals, Inc.; CASTRO, Alfredo C.; CHAN, Katrina; EVANS, Catherine A.; JANARDANANNAIR, Somarajannair; LESCARBEAU, Andre; LI, Liansheng; LIU, Tao; LIU, Yi; REN, Pingda; SNYDER, Daniel A.; TREMBLAY, Martin R.; US2013/267521; (2013); A1;,
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34784-05-9, 6-Bromoisoquinoline is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A solution of 6-bromoisoquinoline (2.08 g, 10 mmol) in dry tetrahydrofuran (20 mL) at -78 C was added dropwise to n-butyl lithium (1 .6 M in hexane, 6.25 mL, 10 mmol) and stirred at -78 C for 15 minutes. The product of Example 3b (770 mg, 5 mmol) in tetrahydrofuran (5 mL) was added and stirred at -78 C for 30 minutes and then slowly warmed to room temperature and stirred for an additional 2 hours. The mixture was quenched with saturated aqueous ammonium chloride and the organics were extracted with ethyl acetate. The combined organic phase was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification of residue by silica gel column chromatography afforded a yellow solid. The solid was recrystallized from petroleum ether and ethyl acetate to give the title compound as a white solid (778 mg, Yield: 55%). Rf = 0.4 (2: 1 petroleum ether/ethyl acetate); 1 H NMR (400 MHz, CDCI3) delta 9.20 (s, 1 H), 8.49 (d, J = 5.6 Hz, 1 H), 7.93-7.90 (m 2 H), 7.64-7.60 (m, 2 H), 5.28 (d, J = 5.6 Hz, 1 H), 2.02 (d, J – 5.6 Hz, 1 H), 1 .91 -1 .88 (m, 1 H), 1 .56-1 .47 (m, 4 H), 1 .37-1 .26 (m, 2 H), 1 .23 (s, 3 H), 1 .12 (s, 3 H), 1 .01 -0.93 (m, 1 H), 0.56 (d, J = 6.4 Hz, 3 H) ppm; Mass spectrum (ESI +ve) m/z 284 (M + H+).

34784-05-9, The synthetic route of 34784-05-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BIKAM PHARMACEUTICALS, INC.; GARVEY, David, S.; GREENWOOD, Jeremy, R.; FRYE, Leah, L.; WO2013/82000; (2013); 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.6624-49-3,Isoquinoline-3-carboxylic acid,as a common compound, the synthetic route is as follows.

General procedure: At 0 ¡ãC and with stirring to the solution of 865 mg (5.0 mmol) of isoquinoline-3-carboxylic acid in 10 ml of anhydrous THF 675 mg (5.0 mmol) of HOBt was added to form reaction mixture A. The solution of 5.5 mmol of l-amino acid benzylester in 5 ml of anhydrous THF was adjusted pH 9 with triethylamine and stirred for 30 min to form mixture B. At 0 ¡ãC the mixtures A and B were mixed and then 1339 mg (6.5 mmol) of DCC was added. The reaction mixture was stirred at 0 ¡ãC for 2 h, at room temperature for12 h and TLC (ethyl acetate/petroleum ether, 1:2) indicated the complete disappearance of isoquinoline-3-carboxylic acid. The formed precipitates of DCU were removed by filtration and the filtrate was evaporated under vacumm. The residue was dissolved in 50 ml of ethyl acetate and the formed solution was washed successively with saturated aqueous solution of NaHCO3 (30 ml .x. 3), 5percent aqueous solution of KHSO4 (30 ml .x. 3) and saturated aqueous solution of NaCl (30 ml .x. 3) and dried over anhydrous Na2SO4. After filtration the filtrate was evaporated under vacumm and the residure was purified on silica gel chromatography (CHCl3:MeOH, 20:1) to give the title compounds., 6624-49-3

Big data shows that 6624-49-3 is playing an increasingly important role.

Reference£º
Article; Zheng, Meiqing; Yang, Yifan; Zhao, Ming; Zhang, Xiaoyi; Wu, Jianhui; Chen, Gong; Peng, Li; Wang, Yuji; Peng, Shiqi; European Journal of Medicinal Chemistry; vol. 46; 5; (2011); p. 1672 – 1681;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

1082674-24-5, 6-Bromoisoquinoline-1-carbonitrile is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 3. Synthesis of 6-amino isoquinoline (#F3). A solution of #F2 (4.5 g, 51.7 mmol), 6-bromoisoquinoline-1-carbonitrile (6.0 g, 25.9 mmol), BINAP (3.2 g, 5.1 mmol), Pd2(dba)3 (2.3 g, 2.6 mmol) and potassium phosphate (11.0 g, 51.7 mmol) in anhydrous DMSO (35 mL) was heated at 80¡ã C. for 2 h. The complete disappearance of the 6-bromoisoquinoline-1-carbonitrile was observed on TLC. The reaction mixture was cooled to room temperature, filtered through a Celite? pad and the filtrate was diluted with water (100 mL). The mixture was extracted with EtOAc (100 mL*3). The combined organic layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure to give crude material. The product was purified by chromatography on silica gel (100-200 mesh) using 10percent MeOH in DCM as eluant to give racemic #F3 as yellow solid (1.5 g, 24.3percent). Rf: 0.4 (50percent EtOAc in petroleum ether). Chiral HPLC: two enantiomers (61.0percent, 39.0percent). LCMS m/z=240.1 (M+H). H NMR (400 MHz, d6-DMSO): delta 2.19-2.27 (m, 1H), 2.36-2.45 (m, 1H), 3.67-3.84 (m, 3H), 4.02-4.07 (m, 1H), 4.33-4.39 (m, 1H), 5.09 (t, J=4.8 Hz, 1H), 6.83 (d, J=1.6 Hz, 1H), 7.33 (dd, J=8.8 Hz, J=2.0 Hz, 1H), 7.78 (d, J=6.4 Hz, 1H), 7.97 (d, J=8.8 Hz, 1H), 8.36 (d, J=5.6 Hz, 1H)., 1082674-24-5

As the paragraph descriping shows that 1082674-24-5 is playing an increasingly important role.

Reference£º
Patent; Pfizer Inc.; Anderson, James Thomas; Chekler, Eugene Lvovich Piatnitski; Ellsworth, Edmund L.; Erickson, Bruce Kipp; Gilbert, Adam Matthew; Ricketts, Anthony P.; Thompson, David P.; Unwalla, Rayomand Jal; Verhoest, Patrick Robert; US2014/155390; (2014); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem