Methanol → N-Cyclopropyl-3-(2-(cyclopropylmethyl)-4-((4-methyl-1,4-diazepan-1-yl)methyl)-1-oxo-1,2-dihydroisoquinolin-6-yl)-5-fluoro-4-methylbenzamide

HRID 907306Notes

Reaction equation

HRID 907306 reaction equation
[CH:1]1([NH:4][C:5](=[O:31])[C:6]2[CH:11]=[C:10]([F:12])[C:9]([CH3:13])=[C:8]([C:14]3[CH:15]=[C:16]4[C:21](=[CH:22][CH:23]=3)[C:20](=[O:24])[N:19]([CH2:25][CH:26]3[CH2:28][CH2:27]3)[CH:18]=[C:17]4[CH:29]=O)[CH:7]=2)[CH2:3][CH2:2]1.[CH3:32][N:33]1[CH2:39][CH2:38][CH2:37][NH:36][CH2:35][CH2:34]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].CO>ClCCl>[CH:1]1([NH:4][C:5](=[O:31])[C:6]2[CH:11]=[C:10]([F:12])[C:9]([CH3:13])=[C:8]([C:14]3[CH:15]=[C:16]4[C:21](=[CH:22][CH:23]=3)[C:20](=[O:24])[N:19]([CH2:25][CH:26]3[CH2:27][CH2:28]3)[CH:18]=[C:17]4[CH2:29][N:36]3[CH2:37][CH2:38][CH2:39][N:33]([CH3:32])[CH2:34][CH2:35]3)[CH:7]=2)[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 887MethanolHCID 2283491-MethylhomopiperazineHCID 5049666Sodium triacetoxyborohydrideHCID 57551841N-Cyclopropyl-3-(2-(cyclopropylmethyl)-4-formyl-1-oxo-1,2-dihydroisoquinolin-6-yl)-5-fluoro-4-methylbenzamide

Product 1

HCID 57551796N-Cyclopropyl-3-(2-(cyclopropylmethyl)-4-((4-methyl-1,4-diazepan-1-yl)methyl)-1-oxo-1,2-dihydroisoquinolin-6-yl)-5-fluoro-4-methylbenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of the product of step i) (0.45 g) in dichloromethane (50 mL) was treated with 1-methyl-1,4-diazepane (0.61 g) and sodium triacetoxyborohydride (0.68 g) and then stirred at room temperature overnight. Methanol (5 mL) was added and the solution purified directly by SiO2 chromatography (eluting with 0 to 20% methanol in dichloromethane) followed by HPLC to give the title compound as a solid (150 mg).

Workup

  1. customthe solution purified directly by SiO2 chromatography (eluting with 0 to 20% methanol in dichloromethane)

Sources & evidence

ORD record
ord-00a4f730627c4c51b9ead44177e15db8
Source dataset
uspto-grants-2011_09
Patent number
US08012979B2

Reaction notes

Loading…