HCID 59497321, compound → HCID 59497365, compound

HRID 1747434Notes

Reaction equation

HRID 1747434 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[C:6]([CH3:11])[CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:12][N:13]2[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[N:15]([C:22]3[CH2:26][CH2:25][CH2:24][C:23]=3[C:27]([OH:29])=[O:28])[C:14]2=[O:30])=[CH:3]1>CO.[Pd]>[CH3:1][N:2]1[C:10]2[C:5](=[C:6]([CH3:11])[CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:12][N:13]2[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[N:15]([CH:22]3[CH2:26][CH2:25][CH2:24][CH:23]3[C:27]([OH:29])=[O:28])[C:14]2=[O:30])=[CH:3]1

Participants

4

Reactant 1

HCID 59497321HCID 59497321, compound

Product 1

HCID 59497365HCID 59497365, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 65 mg (0.16 mmol) of 2-{3-[(1,4-dimethyl-1H-indol-3-yl)methyl]-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl}cyclopent-1-ene-1-carboxylic acid and 30 mg of 10% Pd/C in 3 mL of methanol was stirred at room temperature under hydrogen gas atmosphere (1 atom) for 16 h. The resulting mixture was filtered through Celite and the filtrate was concentrated. The residue was purified by combiflash to give 20 mg (31%) of 2-[3-(1,4-dimethyl-1H-indol-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-cyclopentanecarboxylic acid as a white solid.

Workup

  1. filtrationThe resulting mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by combiflash

Sources & evidence

ORD record
ord-19b71a495c42487ebcce70f42dde8d85
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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