4-Methylbenzaldehyde → HCID 57652578, compound

HRID 1436016Notes

Reaction equation

HRID 1436016 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[NH:15]1[CH2:20][CH2:19][CH:18]([O:21][C:22]2[CH:23]=[C:24]3[C:29](=[CH:30][CH:31]=2)[C:28](=[O:32])[NH:27][CH:26]=[CH:25]3)[CH2:17][CH2:16]1.[CH3:33][C:34]1[CH:41]=[CH:40][C:37]([CH:38]=O)=[CH:36][CH:35]=1>C(O)(=O)C.CN(C)C=O>[CH3:33][C:34]1[CH:41]=[CH:40][C:37]([CH2:38][N:15]2[CH2:16][CH2:17][CH:18]([O:21][C:22]3[CH:23]=[C:24]4[C:29](=[CH:30][CH:31]=3)[C:28](=[O:32])[NH:27][CH:26]=[CH:25]4)[CH2:19][CH2:20]2)=[CH:36][CH:35]=1

Participants

6

Reactant 3

HCID 77254-MethylbenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 15604510SAR407899

Product 1

HCID 57652578HCID 57652578, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6228DimethylformamideSolvent

Procedure

Sodium triacetoxyborohydride (100 mg, 3.9 mol eq) was added to a solution of 6-(piperidin-4-yloxy)-2H-isoquinolin-1-one (30 mg, 0.12 mmol), acetic acid (2 drops) and 4-methylbenzaldehyde (50 μl or 50 mg) in N, N-dimethylformamide (700 μl) and shaken for 17 hours. The reaction was quenched with water and methanol and the product semi-purified using an SCX cartridge. The product was further purified by prep-HPLC to afford 6-[1-(4-Methylbenzyl)piperidin4-yloxy]-2H-isoquinolin-1-one: El-MS: m/z=349.4 [M+H]+.

Workup

  1. customThe reaction was quenched with water and methanol
  2. customThe product was further purified by prep-HPLC

Sources & evidence

ORD record
ord-b7286b1edef5431a97cdb817e208be7b
Source dataset
uspto-grants-2009_11
Patent number
US07618985B2

Reaction notes

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