Lithium Hydroxide → 10-bromo-3((1,3-dimethyl-1H-pyrazol-4-yl)(hydroxy)methyl)-9-fluoro-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxylic acid

HRID 575386Notes

Reaction equation

BrC1C(F)=CC2OCCN3C(C(O)C4C=CC=C(C(F)(F)F)C=4)=C(C(O)=O)N=C3C=2C=1.[Br:32][C:33]1[C:34]([F:60])=[CH:35][C:36]2[O:42][CH2:41][CH2:40][N:39]3[C:43]([CH:50]([C:52]4[C:53]([CH3:58])=[N:54][N:55]([CH3:57])[CH:56]=4)[OH:51])=[C:44]([C:46]([O:48]C)=[O:47])[N:45]=[C:38]3[C:37]=2[CH:59]=1.[OH-].[Li+]>>[Br:32][C:33]1[C:34]([F:60])=[CH:35][C:36]2[O:42][CH2:41][CH2:40][N:39]3[C:43]([CH:50]([C:52]4[C:53]([CH3:58])=[N:54][N:55]([CH3:57])[CH:56]=4)[OH:51])=[C:44]([C:46]([OH:48])=[O:47])[N:45]=[C:38]3[C:37]=2[CH:59]=1

Participants

Reactant 3

HCID 3939Lithium Hydroxide

HCID 8669313310-Bromo-9-fluoro-3-(hydroxy(3-(trifluoromethyl)phenyl)methyl)-5,6-dihydrobenzo[f]imidazo {1,2-d][1,4]oxazepine-2-carboxylic acid

HCID 86693433methyl 10-bromo-3-((1,3-dimethyl-1H-pyrazol-4-yl)(hydroxy)methyl)-9-fluoro-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxylate

Product 1

HCID 8669343410-bromo-3((1,3-dimethyl-1H-pyrazol-4-yl)(hydroxy)methyl)-9-fluoro-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxylic acid

Procedure

10-bromo-3-((1,3-dimethyl-1H-pyrazol-4-yl)(hydroxy)methyl)-9-fluoro-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxylic acid was prepared similarly according to the procedure for the synthesis of 10-bromo-9-fluoro-3-(hydroxy(3-(trifluoromethyl)phenyl)methyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxylic acid. methyl 10-bromo-3-((1,3-dimethyl-1H-pyrazol-4-yl)(hydroxy)methyl)-9-fluoro-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxylate was reacted with lithium hydroxide to the crude title compound which was carried forward without further purification.

Workup

custom10-bromo-3-((1,3-dimethyl-1H-pyrazol-4-yl)(hydroxy)methyl)-9-fluoro-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxylic acid was prepared similarly
customwas carried forward without further purification

Sources & evidence

ORD record: ord-dc5019d9761d426b94e719208f6fd57c
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09034866B2

Reaction notes

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