1-Fluoro-4-(isocyanatomethyl)benzene → N-[(4-Fluorophenyl)methyl]-tetrahydro-3-oxo-1,1-diphenyl-1H-oxazolo[3,4-a][1,4]diazepine-8(5H)-carboxamide

HRID 1713511Notes

Reaction equation

[C:1]1([C:7]2([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:11]3[CH2:12][NH:13][CH2:14][CH2:15][CH2:16][N:10]3[C:9](=[O:17])[O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:24][C:25]1[CH:34]=[CH:33][C:28]([CH2:29][N:30]=[C:31]=[O:32])=[CH:27][CH:26]=1>O1CCCC1>[F:24][C:25]1[CH:26]=[CH:27][C:28]([CH2:29][NH:30][C:31]([N:13]2[CH2:14][CH2:15][CH2:16][N:10]3[C:9](=[O:17])[O:8][C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)([C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH:11]3[CH2:12]2)=[O:32])=[CH:33][CH:34]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To hexahydro-1,1-diphenyl-1H-oxazolo[3,4-a][1,4]diazepin-3-one (60 mg, 0.2 mmol) were added tetrahydrofuran (5 mL) and 4-fluorobenzyl isocyanate (59 mg, 0.39 mmol), and the mixture was stirred at 50° C. for 2 hours. The reaction solution was concentrated under reduced pressure. Then, the residue was purified with silica gel column chromatography (hexane:ethyl acetate=6:1 to hexane:ethyl acetate=1:4) and powder was formed from diethyl ether to obtain the title compound (73 mg, yield 82%).

Workup

concentrationThe reaction solution was concentrated under reduced pressure
customThen, the residue was purified with silica gel column chromatography (hexane:ethyl acetate=6:1 to hexane:ethyl acetate=1:4)
custompowder was formed from diethyl ether

Sources & evidence

ORD record: ord-ca9183dcfb8540fe9b89df160d77a55c
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07795267B2

Reaction notes

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