2-[3-(1,4-dimethyl-3H-indol-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-2-methyl-propionic acid tert-butyl ester → 2-[3-(1,4-dimethyl-3H-indol-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-2-methyl-propionic acid

HRID 1747412Notes

Reaction equation

HRID 1747412 reaction equation
C([O:5][C:6](=[O:32])[C:7]([N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]([CH2:19][CH:20]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][C:27]=3[CH3:29])[N:22]([CH3:30])[CH2:21]2)[C:11]1=[O:31])([CH3:9])[CH3:8])(C)(C)C>C(O)(C(F)(F)F)=O>[CH3:30][N:22]1[C:23]2[C:28](=[C:27]([CH3:29])[CH:26]=[CH:25][CH:24]=2)[CH:20]([CH2:19][N:12]2[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:10]([C:7]([CH3:8])([CH3:9])[C:6]([OH:32])=[O:5])[C:11]2=[O:31])[CH2:21]1

Participants

3

Reactant 1

HCID 673592312-[3-(1,4-dimethyl-3H-indol-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-2-methyl-propionic acid tert-butyl ester

Product 1

HCID 673585622-[3-(1,4-dimethyl-3H-indol-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-2-methyl-propionic acidYield 30%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 2-[3-(1,4-dimethyl-3H-indol-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-2-methyl-propionic acid tert-butyl ester (138 mg, 0.32 mmol) in TFA (1.0 mL) was stirred at room temperature for 1 hour. The reaction mixture was concentrated. The resulting residue was purified by CombiFlash with 10% MeOH in dichloromethane as the eluent to afford the desired 2-[3-(1,4-dimethyl-3H-indol-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-2-methyl-propionic acid (36 mg, 30%). LCMS (ESMS): 378.25 (M+H+).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customThe resulting residue was purified by CombiFlash with 10% MeOH in dichloromethane as the eluent

Sources & evidence

ORD record
ord-34740e1f489447d3bfb3b4923e23b7b0
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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