Tag: 1350643-72-9

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;,
Isoquinoline – Wikipedia
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.

Step 1) (S)-3-(1-aminoethyl)-2-phenyl-8-(prop-1-yn-1-yl)isoquinolin-1(2H)-one To a mixture of (S)-3-(1-aminoethyl)-8-chloro-2-phenylisoquinolin-1(2H)-one (1.5 g, 5.0 mmol) (See the synthetic method of step 1-2 of example 8 in WO2015042078) in DMAC (10 mL) was added Cs2CO3 (2.5 g, 7.7 mmol), PdCl2(PCy3)2(0.38 g, 0.51 mmol). The mixture was purged with N2, then propyne (21 mL, 15 mmol, 3-6% in n-heptane) was added, and the mixture was sealed and heated at 110 C. for 5.5 h. Then the mixture was cooled down to room temperature, added EtOAc (150 mL) and water (30 mL). The organic layer was separated and washed with saturated brine (50 mL*5), dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc/TEA (v/v/v)=1/10/0.5) to give the title compound as a yellow solid (0.81 g, 53%). MS (ESI, pos.ion) m/z: 303.2 [M+H]+; 1H NMR (600 MHz, CDCl3) delta (ppm): 7.60-7.58 (m, 4H), 7.48 (dd, J=15.3, 7.9 Hz, 2H), 7.42 (d, J=7.7 Hz, 1H), 7.34 (d, J=7.4 Hz, 1H), 6.76 (s, 1H), 3.76-3.70 (m, 1H), 2.13 (s, 3H), 1.30 (d, J=6.5 Hz, 3H). 13C NMR (151 MHz, CDCl3) delta (ppm): 162.5, 138.0, 134.1, 131.6, 129.8, 129.7, 129.4, 129.0, 128.9, 125.6, 125.1, 124.7, 102.3, 92.8, 79.9, 46.9, 23.0, 5.4.

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

Reference£º
Patent; Sunshine Lake Pharma Co., Ltd.; Calitor Sciences, LLC; Xi, Ning; Wang, Liang; Feng, Xuejin; Liao, Min; (88 pag.)US2019/224197; (2019); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

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

Example 54 A solution of 2,4-dichloro-5-nitropyrimidine (250 mg, 1.29 mmol, 1.15 eq.) in THF (2 mL) was chilled in a -78 C. bath. To this solution was slowly added over 40 mins a mixture of compound 1 (335 mg, 1.12 mmol, 1.0 eq.) and DIEA (450 muL, 2.58 mmol, 2.3 eq.) in THF (4 mL). After addition was complete, the reaction was stirred at -78 C. during 30-40 mins, then allowed to warm slowly to 15 C. over 1 h. The reaction mixture was diluted with DCM (40 mL), washed with water and brine (15 mL each), dried over Na2SO4, and concentrated. This residue was purified by flash chromatography eluting with 300 mL each 10/20/30/40% EtOAc/hexanes to give (S)-8-chloro-3-(1-(2-chloro-5-nitropyrimidin-4-ylamino)ethyl)-2-phenylisoquinolin-1(2H)-one 75. ESI-MS 456.15 [M+H]+.

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; INTELLKINE, LLC; INFINITY PHARMACEUTICALS, INC.; CASTRO, Alfredo C.; EVANS, Catherine A.; JANARDANANNAIR, Somarajannair; LESCARBEAU, Andre; LIU, Tao; SNYDER, Daniel A.; TREMBLAY, Martin R.; REN, Pingda; LIU, Yi; LI, Liansheng; CHAN, Katrina; US2013/53362; (2013); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

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

[00721] To a mixture of amine (D-i) (1.0 eq, e.g., 0.5 mmol), Wd-COOH carboxylic acid (1.1 eq, e.g., 0.55 mmol), and N,N-diisopropylethylamine (2.0 eq, e.g., 0.17 mL, 1.0 mmol) in anhydrous DMF (e.g., 5 mL), 1- hydroxybenzotriazole hydrate (1.3 eq, e.g., 0.65 mmol) and EDC hydrochloride (1.3 eq, e.g., 0.65 mmol,) are added sequentially and the resulting mixture is stirred at RT for 2-i 6 h. Ice-water or saturated sodium carbonate solution is added to the reaction mixture and then stirred for 10 mm. The precipitate is collected by filtration, rinsed with water and dried in vacuo. The solid collected is further purified by flash column chromatography on silica gel (e.g., 0-i 0% MeOH-DCM) to afford the product amide (D-2). [00748] Compound 1 was prepared according to Method A. It was then coupled to 3-amino-6- bromopyrazine-2-carboxylic acid using Method D to provide compound 2 which was converted to compound 3 according to the following procedure: A 25 mL microwave tube was charged with compound 2 (0.35 mmol, 1.0 equiv), potassium cyclpropyltrifluoroborate (2 equiv) and sodium carbonate (3 equiv) and placed under Ar. A solution of dioxane/water (5 mL, 4:1 v/v) was added and the mixture was bubbled with Argon for 5 mm. PdC12(amphos)2 (10 mol%) was then added and bubbled with Ar for an additional 5 mm. The reaction was then sealed and heated to 90 oC for 3h after which there was no more SM by LC/MS analysis. The reaction was then partionned between methylene chlroide and water. The aqeuous layer was extracted with methylene chloride (2x). The organic layers were combined, dried over Na2504 and concentrated. This material was further purified by HPLC (10-60% methanol/0.1% trifluoroacetic acid in water) to provide compound 3. ESI-MS m/z: 460.4 [M+H]t

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; INFINITY PHARMACEUTICALS, INC.; CASTRO, Alfredo, C.; EVANS, Catherine, A.; JANARDANANNAIR, Somarajannair; LESCARBEAU, Andre; LIU, Tao; TREMBLAY, Martin, R.; WO2015/51241; (2015); 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.1350643-72-9,(S)-3-(1-Aminoethyl)-8-chloro-2-phenylisoquinolin-1(2H)-one,as a common compound, the synthetic route is as follows.

To a solution of 60 mg (0.221 mmol) of tert-butyl 4-chloro-6,7-dihydro-8H-pyrimido [5,4- b] [1,4] oxazine-8-carboxylate in a 5 mL microwave vial, 73 mg (0.243 mmol) of (S) -3- (1-aminoethyl) -8-chloro-2-phenylisoquinoline-1 (2H) -one obtained in Preparation Example 3 was dissolved in 3 mL of anhydrous toluene , 1.5 mg (0.007 mmol) of palladium (II) acetate (Pd (OAc) 2) 2,2′-bis (diphenylphosphino) -1,1′-binaphthalene ((+ -) – BINAP) 12 mg (0.020 mmol), 101 mg (0.309 mmol) of cesium carbonate (Cs2CO3) was added and the degassing was performed three times using argon gas. Followed by stirring at 80 C for 24 hours. The reaction mixture was filtered under reduced pressure, and the organic layer was extracted with ethyl acetate and water. The organic layer was dried (Na2SO4), filtered and concentrated. The crude product was dissolved in dichloromethane and purified by column chromatography (SiO2, eluent: hexane (20% ethyl acetate in hexane) to give tert-butyl (S)-4-((1-(8-chloro-1-oxo-2-phenyl-1,2-dihydroisoquinolin-3-yl)ethyl)amino)6,7-dihydro-8H-pyrimido[5,4-b][1,4]oxazine-8-carboxylate 50 mg (0.094 mmol, 42% yield) was obtained as a pale yellow solid.

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; Korea Research Institute of Chemical Technology; Lee, Gay Hyung; Lim, Hee Jong; Cho, Hee Young; Park, Woo Kyu; Jung, Dae Young; (40 pag.)KR2017/74381; (2017); A;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem