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

HRID 575391Notes

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[S:23][CH:22]=[N:21][C:20]=4[CH3:24])=[C:13]([C:15](O)=[O:16])[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[S:23][CH:22]=[N:21][C:20]=4[CH3:24])=[C:13]([C:15]([NH2:29])=[O:16])[N:14]=[C:7]3[C:6]=2[CH:26]=1

Participants

Reactant 2

HCID 25517Ammonium Chloride

HCID 8669343810-Bromo-9-fluoro-3-[hydroxy-(4-methylthiazol-5-yl)methyl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2-carboxylic acid

Product 1

HCID 8669343910-Bromo-9-fluoro-3-[hydroxy-(4-methylthiazol-5-yl)methyl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2-carboxamideYield 15%

Procedure

10-bromo-9-fluoro-3-[hydroxy-(4-methylthiazol-5-yl)methyl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2-carboxylic acid was reacted with ammonium chloride and purified by flash chromatography to afford 30.4 mg (15% yield) of the title compound.

Workup

custompurified by flash chromatography

Sources & evidence

ORD record: ord-860764cc21cb45788036540f20540142
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09034866B2

Reaction notes

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