Water → 6-(azepan-4-yloxy)-2-(4-methoxy-benzyl)-7-methyl-2H-isoquinolin-1-one

HRID 1255426Notes

Reaction equation

HRID 1255426 reaction equation
[NH:1]1[CH2:7][CH2:6][CH2:5][CH:4]([OH:8])[CH2:3][CH2:2]1.[H-].[Na+].F[C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][C:21]=1[CH3:22])[C:18](=[O:23])[N:17]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=1)[CH:16]=[CH:15]2.O>CC(N(C)C)=O>[NH:1]1[CH2:7][CH2:6][CH2:5][CH:4]([O:8][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][C:21]=2[CH3:22])[C:18](=[O:23])[N:17]([CH2:24][C:25]2[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=2)[CH:16]=[CH:15]3)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydride2×HCID 5149746Azepan-4-ol2×HCID 592260436-fluoro-2-(4-methoxybenzyl)-7-methylisoquinolin-1(2H)-one2×

Product 1

HCID 685558126-(azepan-4-yloxy)-2-(4-methoxy-benzyl)-7-methyl-2H-isoquinolin-1-oneYield 41%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent2×

Procedure

A solution of 58 mg (0.51 mmol) azepan-4-ol in 5 ml dimethylacetamide was stirred with 45 mg (1.52 mmol) 80 percent sodium hydride for 45 minutes at room temperature. Then 150 mg (0.51 mmol) 6-fluoro-2-(4-methoxy-benzyl)-7-methyl-2H-isoquinolin-1-one in dimethylacetamide was added. The reaction mixture was heated to 80° C. for 3 days during which additional amounts of azepan-4-ol and sodium hydride were added until complete conversion of the 6-fluoro-2-(4-methoxy-benzyl)-7-methyl-2H-isoquinolin-1-one was obtained. The reaction mixture was slowly added to 10 ml water and after 1 h of stirring the product was isolated by filtration and dried overnight in vacuum. 82 mg of 6-(azepan-4-yloxy)-2-(4-methoxy-benzyl)-7-methyl-2H-isoquinolin-1-one were obtained.

Workup

  1. customwas obtained
  2. customwas isolated by filtration
  3. customdried overnight in vacuum

Sources & evidence

ORD record
ord-3189be881a914221a01c1c9749df9cb0
Source dataset
uspto-grants-2013_06
Patent number
US08461144B2

Reaction notes

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