Ammonium Chloride → (+/-)-10-Bromo-9-fluoro-3-[hydroxy-(2-methylpyrazol-3-yl)methyl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2-carboxamide

HRID 575379Notes

Reaction equation

[Br:1][C:2]1[C:3]([F:27])=[CH:4][C:5]2[O:11][CH2:10][CH2:9][N:8]3[C:12]([CH:18]([OH:25])[C:19]4[N:23]([CH3:24])[N:22]=[CH:21][CH:20]=4)=[C:13]([C:15]([OH:17])=O)[N:14]=[C:7]3[C:6]=2[CH:26]=1.[Cl-].[NH4+:29]>>[Br:1][C:2]1[C:3]([F:27])=[CH:4][C:5]2[O:11][CH2:10][CH2:9][N:8]3[C:12]([CH:18]([OH:25])[C:19]4[N:23]([CH3:24])[N:22]=[CH:21][CH:20]=4)=[C:13]([C:15]([NH2:29])=[O:17])[N:14]=[C:7]3[C:6]=2[CH:26]=1

Participants

Reactant 2

HCID 25517Ammonium Chloride

HCID 8669342610-bromo-9-fluoro-3-(hydroxy(1-methyl-1H-pyrazol-5-yl)methyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxylic acid

Product 1

HCID 86693427(+/-)-10-Bromo-9-fluoro-3-[hydroxy-(2-methylpyrazol-3-yl)methyl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2-carboxamideYield 50%

Procedure

10-bromo-9-fluoro-3-(hydroxy(1-methyl-1H-pyrazol-5-yl)methyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxylic acid was reacted with ammonium chloride and purified by flash chromatography to afford 79 mg (50% yield) of the title compound.

Workup

custompurified by flash chromatography

Sources & evidence

ORD record: ord-7e66dc76a4604e9a9b1fc54d475b2ddf
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09034866B2

Reaction notes

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