4-[3-(1,4-dimethyl-3H-indol-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-pentanoic acid methyl ester → 4-{3-[(1,4-dimethyl-1H-indol-3-yl)methyl]-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl}pentanoic acid
Reaction equation
C[O:2][C:3](=[O:30])[CH2:4][CH2:5][CH:6]([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]([CH2:17][CH:18]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][C:25]=3[CH3:27])[N:20]([CH3:28])[CH2:19]2)[C:9]1=[O:29])[CH3:7]>O1CCOCC1.O>[CH3:28][N:20]1[C:21]2[C:26](=[C:25]([CH3:27])[CH:24]=[CH:23][CH:22]=2)[C:18]([CH2:17][N:10]2[C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:8]([CH:6]([CH3:7])[CH2:5][CH2:4][C:3]([OH:30])=[O:2])[C:9]2=[O:29])=[CH:19]1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 4-[3-(1,4-dimethyl-3H-indol-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-pentanoic acid methyl ester (120 mg, 0.3 mmol) in dioxane (2.5 ml) was added a solution of LiOH monohydrate (25 mg, 0.6 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 (250 □L) and concentrated. The resulting residue was purified by CombiFlash with 10% MeOH in dichloromethane as the eluent to afford the desired 4-{3-[(1,4-dimethyl-1H-indol-3-yl)methyl]-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl}pentanoic acid (17 mg, 15%). LCMS (ESMS): 392.26 (M+H+).
Workup
- customThe reaction mixture was quenched with 4M HCl in dioxane (250 □L)
- concentrationconcentrated
- customThe resulting residue was purified by CombiFlash with 10% MeOH in dichloromethane as the eluent
Sources & evidence
- ORD record
- ord-20b57392c53148cab9931dfff23a1d90
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09150556B2
Reaction notes
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