Lithium Hydroxide → 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

HRID 575378Notes

Reaction equation

HRID 575378 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:59])=[CH:35][C:36]2[O:42][CH2:41][CH2:40][N:39]3[C:43]([CH:50]([OH:57])[C:51]4[N:52]([CH3:56])[N:53]=[CH:54][CH:55]=4)=[C:44]([C:46]([O:48]C)=[O:47])[N:45]=[C:38]3[C:37]=2[CH:58]=1.[OH-].[Li+]>>[Br:32][C:33]1[C:34]([F:59])=[CH:35][C:36]2[O:42][CH2:41][CH2:40][N:39]3[C:43]([CH:50]([OH:57])[C:51]4[N:52]([CH3:56])[N:53]=[CH:54][CH:55]=4)=[C:44]([C:46]([OH:48])=[O:47])[N:45]=[C:38]3[C:37]=2[CH:58]=1

Participants

4

Reactant 3

HCID 3939Lithium HydroxideHCID 8669313310-Bromo-9-fluoro-3-(hydroxy(3-(trifluoromethyl)phenyl)methyl)-5,6-dihydrobenzo[f]imidazo {1,2-d][1,4]oxazepine-2-carboxylic acidHCID 86693425Methyl 10-bromo-9-fluoro-3-[hydroxy-(2-methylpyrazol-3-yl)methyl]-5,6-dihydroimidazo[1,2-d][1,4]benz oxazepine-2-carboxylate

Product 1

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 acidYield 87%

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 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-9-fluoro-3-[hydroxy-(2-methylpyrazol-3-yl)methyl]-5,6-dihydroimidazo[1,2-d][1,4]benz oxazepine-2-carboxylate was reacted with lithium hydroxide to afford 160 mg (87% yield) of the title compound.

Workup

  1. custom10-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 prepared similarly

Sources & evidence

ORD record
ord-28f85867a4154c8d9f129a447a6ed19d
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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