Lithium Hydroxide → 1-(3-Methoxy-benzyl)-2-[4-(3-oxo-morpholin-4-yl)-phenylcarbamoyl]-1H-benzoimidazole-4-carboxylic acid

HRID 18552Notes

Reaction equation

C[O:2][C:3]([C:5]1[C:13]2[N:12]=[C:11]([C:14](=[O:29])[NH:15][C:16]3[CH:21]=[CH:20][C:19]([N:22]4[CH2:27][CH2:26][O:25][CH2:24][C:23]4=[O:28])=[CH:18][CH:17]=3)[N:10]([CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([O:37][CH3:38])[CH:32]=3)[C:9]=2[CH:8]=[CH:7][CH:6]=1)=[O:4].[Li+].[OH-]>CO>[CH3:38][O:37][C:33]1[CH:32]=[C:31]([CH:36]=[CH:35][CH:34]=1)[CH2:30][N:10]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([C:3]([OH:4])=[O:2])[C:13]=2[N:12]=[C:11]1[C:14](=[O:29])[NH:15][C:16]1[CH:17]=[CH:18][C:19]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][C:23]2=[O:28])=[CH:20][CH:21]=1

Participants

Conditions

Temperature: 60 °C

Procedure

20 mg (0.04 mmol) 1-(3-Methoxy-benzyl)-2-[4-(3-oxo-morpholin-4-yl)-phenylcarbamoyl]-1H-benzoimidazole-4-carboxylic acid methyl ester were suspended in 5 mL MeOH. 194 μl (0.19 mmol) of an aqueous 1 M LiOH-solution were added and the resulting mixture was stirred for 8 h at 60° C. After acidification with a 1 M HCL-solution the mixture was concentrated. The resulting residue was purified by preparative HPLC (CH3CN/H2O gradient+0.05% formic acid) to give pure 1-(3-Methoxy-benzyl)-2-[4-(3-oxo-morpholin-4-yl)-phenylcarbamoyl]-1H-benzoimidazole-4-carboxylic acid as a colorless amorphous solid. Yield: 44 mg MS (ES+): m/e=501.

Workup

concentrationAfter acidification with a 1 M HCL-solution the mixture was concentrated
customThe resulting residue was purified by preparative HPLC (CH3CN/H2O gradient+0.05% formic acid)

Sources & evidence

ORD record: ord-b856a0d71a79491b9506c65e836cc788
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07741341B2

Reaction notes

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