Lithium Hydroxide → 10-Bromo-3-((3,5-difluorophenyl)(hydroxy)methyl)-9-fluoro-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxylic acid
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:61])=[CH:35][C:36]2[O:42][CH2:41][CH2:40][N:39]3[C:43]([CH:50]([C:52]4[CH:57]=[C:56]([F:58])[CH:55]=[C:54]([F:59])[CH:53]=4)[OH:51])=[C:44]([C:46]([O:48]C)=[O:47])[N:45]=[C:38]3[C:37]=2[CH:60]=1.[OH-].[Li+]>>[Br:32][C:33]1[C:34]([F:61])=[CH:35][C:36]2[O:42][CH2:41][CH2:40][N:39]3[C:43]([CH:50]([C:52]4[CH:57]=[C:56]([F:58])[CH:55]=[C:54]([F:59])[CH:53]=4)[OH:51])=[C:44]([C:46]([OH:48])=[O:47])[N:45]=[C:38]3[C:37]=2[CH:60]=1Participants
4
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 86693429Methyl 10-bromo-3-((3,5-difluorophenyl)(hydroxy)methyl)-9-fluoro-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxylateProduct 1
Procedure
10-bromo-3-((3,5-difluorophenyl)(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-((3,5-difluorophenyl)(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-((3,5-difluorophenyl)(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-9b1db3d13c0f4ddca27a6dc2b1a6ba8c
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09034866B2
Reaction notes
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