10-Bromo-9-fluoro-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide → (+/-)-10-(4-(Azetidin-1-yl)-3-hydroxy-3-methyl-4-oxobut-1-yn-1-yl)-9-fluoro-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide

HRID 575188Notes

Reaction equation

HRID 575188 reaction equation
Br[C:2]1[C:3]([F:19])=[CH:4][C:5]2[O:11][CH2:10][CH2:9][N:8]3[CH:12]=[C:13]([C:15]([NH2:17])=[O:16])[N:14]=[C:7]3[C:6]=2[CH:18]=1.[N:20]1([C:24](=[O:30])[C:25]([OH:29])([CH3:28])[C:26]#[CH:27])[CH2:23][CH2:22][CH2:21]1>>[N:20]1([C:24](=[O:30])[C:25]([OH:29])([CH3:28])[C:26]#[C:27][C:2]2[C:3]([F:19])=[CH:4][C:5]3[O:11][CH2:10][CH2:9][N:8]4[CH:12]=[C:13]([C:15]([NH2:17])=[O:16])[N:14]=[C:7]4[C:6]=3[CH:18]=2)[CH2:21][CH2:22][CH2:23]1

Participants

3

Reactant 2

HCID 8669305110-Bromo-9-fluoro-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamideHCID 866931971-(Azetidin-1-yl)-2-hydroxy-2-methylbut-3-yn-1-one

Product 1

HCID 71715105(+/-)-10-(4-(Azetidin-1-yl)-3-hydroxy-3-methyl-4-oxobut-1-yn-1-yl)-9-fluoro-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamideYield 22%

Procedure

Similar to as described in General Procedure G, 10-bromo-9-fluoro-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide was reacted with 1-(azetidin-1-yl)-2-hydroxy-2-methylbut-3-yn-1-one to give the titled compound as a yellow solid (40 mg, 22%).

Sources & evidence

ORD record
ord-5dc3ca5b835f40058a422d82a8eacc0a
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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