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

HRID 575203Notes

Reaction equation

HRID 575203 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.[CH3:20][N:21]1[CH:25]=[CH:24][N:23]=[C:22]1[C:26]([OH:30])([C:28]#[CH:29])[CH3:27]>>[F:19][C:3]1[C:2]([C:29]#[C:28][C:26]([OH:30])([C:22]2[N:21]([CH3:20])[CH:25]=[CH:24][N:23]=2)[CH3:27])=[CH:18][C:6]2[C:7]3[N:8]([CH:12]=[C:13]([C:15]([NH2:17])=[O:16])[N:14]=3)[CH2:9][CH2:10][O:11][C:5]=2[CH:4]=1

Participants

3

Reactant 2

HCID 8669305110-Bromo-9-fluoro-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamideHCID 866930882-(1-methyl-1H-imidazol-2-yl)but-3-yn-2-ol

Product 1

HCID 86693210(+/-)-9-fluoro-10-(3-hydroxy-3-(1-methyl-1H-imidazol-2-yl)but-1-yn-1-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamideYield 16%

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 2-(1-methyl-1H-imidazol-2-yl)but-3-yn-2-ol to give the titled compound as an off-white solid (22 mg, 16%).

Sources & evidence

ORD record
ord-f496b1fc5bd4435a88a870ac0ab47e90
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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