Water → HCID 66965767, compound

HRID 1515016Notes

Reaction equation

HRID 1515016 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[NH2:21])[C:5]([NH:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][N:9]=1)=[O:6].[CH3:22][O:23][C:24](=[O:37])[CH2:25][CH2:26][C:27]1[CH:32]=[C:31]([CH3:33])[C:30]([CH:34]=O)=[C:29]([CH3:36])[CH:28]=1.OOS([O-])=O.[K+].O>CN(C=O)C>[CH3:22][O:23][C:24](=[O:37])[CH2:25][CH2:26][C:27]1[CH:32]=[C:31]([CH3:33])[C:30]([C:34]2[NH:1][C:2]3[CH:3]=[C:4]([C:5](=[O:6])[NH:7][C:8]4[C:17]5[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=5)[CH:11]=[CH:10][N:9]=4)[CH:18]=[CH:19][C:20]=3[N:21]=2)=[C:29]([CH3:36])[CH:28]=1

Participants

6

Reactant 4

HCID 962WaterHCID 23707502Potassium hydroxy sulfiteHCID 54209618Methyl 3-(3,5-dimethyl-4-formylphenyl)propionateHCID 66966238HCID 66966238, compound

Product 1

HCID 66965767HCID 66965767, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3,4-diamino-N-isoquinolin-1-yl-benzamide (200 mg) and 3-(4-formyl-3,5-dimethylphenyl)-propionic acid methyl ester (189 mg) (from Example 6-17) in 5 mL DMF/0.5 mL water was stirred at ambient temperature for 15 min then oxone (292 mg) was added and stirring was continued for 1 h. Water was added and the mixture was extracted with EtOAc. The organic phase was dried over sodium sulfate and the solvent was removed under reduced pressure. The residue was purified by flash chromatography using 5% MeOH/methylene chloride as eluent to give 3-{4-[6-(Isoquinolin-1-ylcarbamoyl)-1H-benzoimidazol-2-yl]-3,5-dimethylphenyl}-propionic acid methyl ester. MS (ESI)m/z 479.1 (M+H), retention time=1.33 min, Method 10.

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. customthe solvent was removed under reduced pressure
  4. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-cf6349103fc74d49956f0e4f509c7c41
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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