Water → N-[(3RS)-1-(3-azabicyclo[3.2.2]non-3-yl)carbonylmethyl-2,3-dihydro-5-(2-fluorophenyl)-2-oxo-1H-1,4-benzodiazepin-3-yl]-N'-(3-hydroxymethylphenyl)urea

HRID 963522

Reaction equation

[CH:1]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][N:3]([C:10]([CH2:12][N:13]1[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[C:17]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[F:30])=[N:16][CH:15]([NH:31][C:32]([N:34]3[CH:38]=[CH:37]N=C3)=[O:33])[C:14]1=[O:39])=[O:11])[CH2:2]2.N[C:41]1[CH:42]=[C:43]([CH:46]=CC=1)[CH2:44][OH:45].C(OCC)(=O)C.O>CN(C)C=O>[CH:5]12[CH2:8][CH2:9][CH:1]([CH2:7][CH2:6]1)[CH2:2][N:3]([C:10]([CH2:12][N:13]1[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[C:17]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[F:30])=[N:16][CH:15]([NH:31][C:32]([NH:34][C:38]3[CH:37]=[CH:41][CH:42]=[C:43]([CH2:44][OH:45])[CH:46]=3)=[O:33])[C:14]1=[O:39])=[O:11])[CH2:4]2

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of [(3RS)-1-(3-azabicyclo[3.2.2]non-3-yl)carbonylmethyl-2,3-dihydro-3-(imidazol-1-yl)carbonylamino-5-(2-fluoro-phenyl)-1H-1,4-benzodiazepin-2-one (500 mg) and 3-aminobenzyl alcohol (128 mg) in dimethylformamide (5.0 ml) was stirred at 100° C. for 5 hours. Ethyl acetate and water were added to the reaction mixture at room temperature, and organic layer was separated, washed with water and brine, dried over magnesium sulfate, and isolated by column chlomatography on silica gel to afford N-[(3RS)-1-(3-azabicyclo[3.2.2]non-3-yl)carbonylmethyl-2,3-dihydro-5-(2-fluorophenyl)-2-oxo-1H-1,4-benzodiazepin-3-yl]-N'- (3-hydroxymethylphenyl)urea.

Workup

customorganic layer was separated
washwashed with water and brine
dry with materialdried over magnesium sulfate
customisolated by column chlomatography on silica gel

Sources & evidence

ORD record: ord-1f1eca8846fd44a6b8621269e67df73b
Source dataset: uspto-grants-1998_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05763437

Linked notes

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