Category: 23707-37-1

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.23707-37-1,Isoquinolin-7-amine,as a common compound, the synthetic route is as follows.

7-Aminoisoquinoline (6.26 g, 43.4 mmol) (J. Chem. Soc.1951, 2851) is added to 40 mL of concentrated hydrochloric acid at 0C. Sodium nitrite (3.0 g, 43.4 mmol) is dissolved in 15 mL water, cooled to 0C, and added dropwise to the isoquinoline solution. The reaction is stirred for 30 min at 0C. Stannous chloride dihydrate (29.3 g, 130.2 mmol, 3 eq) is dissolved in 25 mL concentrated hydrochloric acid, the solution cooled to 0C, and added dropwise to the isoquinoline solution. The reaction is placed in the refrigerator overnight. The next day the precipitate is isolated by filtration, washed with 100 mL ice cold brine followed by 100 mL of a 2:1 petroleum ether/ethyl ether solution. The brown solid is dried under dynamic vacuum overnight. The tin double salt of the isoquinoline (9.0 g, 26 mmol) is suspended in 100 mL glacial acetic acid and ethyl 2,4-dioxopentanoate oxime (4.0 g, 21.3 mmol) added dropwise. The reaction was brought to reflux overnight. The next day the acetic acid was evaporated and to the residue was added 100 mL water, cooled to 0C and neutralized with solid sodium bicarbonate. The solution was extracted with ethyl acetate (6×50 mL), dried over sodium sulfate, and evaporated to give the title compound as a brownish solid (5.15 g, 86% yield) which was >85% of the desired pyazole regioisomer. The material may be purified by silica gel flash chromatography eluting with 5% methanol in chloroform: 1H NMR (CDCl3) delta 1.24 (t, 3H, J=7.1 Hz, OCH2CH3), 2.40 (s, 3H, pyrazole CH3), 4.24 (q, 2H, J=7.1 Hz, OCH2CH3), 6.89 (s, 1H, pyrazole H), 7.70 (d, 1H, J=5.9 Hz, H4), 7.75 (dd, 1H, J=8.8 Hz, J=2.2 Hz, H6), 7.89 (d, 1H, J=8.8 Hz, H5), 8.05 (d, 1H, J=2.0 Hz, H7), 8.58 (s, 1H, J=5.9 Hz, H3), 9.29 (s, 1H, H1), MS (ES+): 282.1 (M+H)+ (100%), C30H29N5O3S 539.65., 23707-37-1

23707-37-1 Isoquinolin-7-amine 14660277, aisoquinoline compound, is more and more widely used in various fields.

Reference£º
Patent; Bristol-Myers Squibb Pharma Company; EP991638; (2005); B1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

23707-37-1, Isoquinolin-7-amine is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

7-Aminoisoquinoline (4.81 g, 33.4 mmol) (J. Chem. Soc. 1951, 2851) was dissolved in 100 mL of dichloromethane under a nitrogen atmosphere. Triethylamine (5.60 mL, 40.2 mmol, 1.2 eq.) was added to the isoquinoline solution. Ethyl oxalylchloride (4.10 mL, 36.7 mmol, 1.1 eq.) was added dropwise over 30 minutes and the reaction was stirred for 60 min. at ambient temperature. The solution was diluted with 100 mL of dichloromethane, washed with water (2¡Á50 mL) and brine (1¡Á50 mL), filtered through phase separatory paper, and evaporated to give a pale yellow solid. This solid was dissolved in 50 mL of dichloromethane and hexanes (100 mL) was added. The resulting precipitate was isolated by filtration and dried under vacuum to give [(isoquinol-7′-yl)amino]-oxoacetic acid, ethyl ester as an off-white solid (7.60 g, 93% yield). 1H NMR (CDCl3) delta1.47 (t, 3H, J=7.1 Hz, OCH2CH3), 4.47 (q, 2H, J=7.2 Hz, OCH2CH3), 7.63 (d, 1H, J=5.5 Hz, aromatic H), 7.78 (dd, 1H, J=8.9 Hz, J=2.0 Hz, aromatic H), 7.86 (d, 1H, J=8.8 Hz, aromatic H), 8.50 (d, 1H, J=19 Hz, aromatic H), 8.52 (d, 1H, J=5.8 Hz, aromatic H), 9.13 (bs, 1H, NH), 9.27 (s, 1H, aromatic H). C13H12N2O3 244.25, 23707-37-1

As the paragraph descriping shows that 23707-37-1 is playing an increasingly important role.

Reference£º
Patent; DuPont Pharmaceuticals Company; US6339099; (2002); B1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

23707-37-1, Isoquinolin-7-amine is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a mixture of 7-[(2-chloro-pyridine-3-carbonyl)-amino]-4,4-dimethyl-3,4-dihydro-lH-isoquinoline-2-carboxylicacid tert-butyl ester (20.8 g, 50 mmol, 1.0 eq.), 7-aminoisoquinoline (7.2 g, 50 mmol, 1.0 eq.), Pd2(dba)3 (915mg, lmmol,0.02 eq), 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl (CASNo. 213697-53-1, Strem Chemicalscat no. 15-1145; 785 mg, 2 mmol, 0.04 eq) under N2 in a 250mL pressure reaction vessel was added 1.0 M LiNTMS2 THFsolution (120 mL, 120 mmol, 2.4 eq.). The reaction vesselwas sealed with a Teflon screwcap and the mixture wasstirred at 70 SC for 17 h. The mixture was then cooled toRT. 100 mL of water was added to the mixture and the mixturewas extracted with 500 mL of EtOAc. The organic layer waswashed with sat. NH4C1 solution, 1M NaHP04 solution (4x200mL) then dried over MgS04. After filtration andconcentration, the crude was purified through a silica gelcolumn chroma tography, eluting with CH2Cl2/EtOAc. Thedesired title compound was obtained as a yellow solid. MS(ES+) : 524 (M+H) + . Calc’d for CsiHssNsOs- 523.26, 23707-37-1

As the paragraph descriping shows that 23707-37-1 is playing an increasingly important role.

Reference£º
Patent; AMGEN INC.; WO2006/12374; (2006); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem