{1-[3-(1,4-dimethyl-3H-indol-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-cyclohexyl}-acetic acid methyl ester → {1-[3-(1,4-Dimethyl-1H-indol-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl)-cyclohexyl}-acetic acid

HRID 1747403Notes

Reaction equation

HRID 1747403 reaction equation
C[O:2][C:3](=[O:33])[CH2:4][C:5]1([N:11]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[N:13]([CH2:20][CH:21]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][C:28]=4[CH3:30])[N:23]([CH3:31])[CH2:22]3)[C:12]2=[O:32])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1>O1CCOCC1.O>[CH3:31][N:23]1[C:24]2[C:29](=[C:28]([CH3:30])[CH:27]=[CH:26][CH:25]=2)[C:21]([CH2:20][N:13]2[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N:11]([C:5]3([CH2:4][C:3]([OH:33])=[O:2])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]3)[C:12]2=[O:32])=[CH:22]1

Participants

4

Reactant 1

HCID 67359481{1-[3-(1,4-dimethyl-3H-indol-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-cyclohexyl}-acetic acid methyl ester

Product 1

HCID 25124207{1-[3-(1,4-Dimethyl-1H-indol-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl)-cyclohexyl}-acetic acidYield 68%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of {1-[3-(1,4-dimethyl-3H-indol-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-cyclohexyl}-acetic acid methyl ester (131 mg, 0.29 mmol) in dioxane (2.5 ml) was added a solution of LiOH monohydrate (25 mg, 0.60 mmol) in H2O (2.5 mL). The solution was stirred at room temperature for 4 hours. The reaction mixture was quenched with 4M HCl in dioxane (500 □L) and concentrated. The resulting residue was purified by CombiFlash with 3% MeOH in dichloromethane as the eluent to afford the desired {1-[3-(1,4-Dimethyl-1H-indol-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-cyclohexyl}-acetic acid (85 mg, 68%). LCMS (ESMS): 432.32 (M+H+).

Workup

  1. customThe reaction mixture was quenched with 4M HCl in dioxane (500 □L)
  2. concentrationconcentrated
  3. customThe resulting residue was purified by CombiFlash with 3% MeOH in dichloromethane as the eluent

Sources & evidence

ORD record
ord-f2051acabc264b8399367957e765c18e
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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