Water → HCID 22175536, compound

HRID 1797659Notes

Reaction equation

HRID 1797659 reaction equation
C1C2C(COC(=O)[NH:17][CH2:18][C:19]3[N:20]([CH2:42][CH:43]([CH3:45])[CH3:44])[C:21](=[O:41])[C:22]4[C:27]([C:28]=3[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[CH:26][C:25]([C:35]3[S:36][CH:37]=[C:38]([CH3:40])[N:39]=3)=[CH:24][CH:23]=4)C3C(=CC=CC=3)C=2C=CC=1.N1CCCC1.O>CN(C)C=O>[NH2:17][CH2:18][C:19]1[N:20]([CH2:42][CH:43]([CH3:45])[CH3:44])[C:21](=[O:41])[C:22]2[C:27]([C:28]=1[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[CH:26][C:25]([C:35]1[S:36][CH:37]=[C:38]([CH3:40])[N:39]=1)=[CH:24][CH:23]=2

Participants

5

Reactant 3

HCID 962WaterHCID 31268PyrrolidineHCID 22175631HCID 22175631, compound

Product 1

HCID 22175536HCID 22175536, compoundYield 54.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 9H-fluoren-9-ylmethyl[2-isobutyl-6-(4-methyl-1,3-thiazol-2-yl)-1-oxo-4-phenyl-1,2-dihydro-3-isoquinolinyl]methylcarbamate (0.38 g, 0.6 mmol) in N,N-dimethylformamide (10 ml) was added pyrrolidine (0.5 ml) and the mixture was stirred at room temperature for 1 h. The reaction mixture was poured into water and extracted with ethyl acetate. The residue was purified by silica gel column chromatography to give 3-(aminomethyl)-2-isobutyl-6-(4-methyl-1,3-thiazol-2-yl)-4-phenyl-1(2H)-isoquinolinone (0.13 g, 54.2%) as crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9b5c24360eaa4f56a70236a37420e34a
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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