10-Bromo-9-fluoro-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide → 9-Fluoro-10-(3-(5-formylisoxazol-3-yl)-3-hydroxybut-1-yn-1-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide

HRID 575228Notes

Reaction equation

HRID 575228 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.[OH:20][C:21]([C:25]1[CH:29]=[C:28]([CH:30]=[O:31])[O:27][N:26]=1)([C:23]#[CH:24])[CH3:22]>>[F:19][C:3]1[C:2]([C:24]#[C:23][C:21]([C:25]2[CH:29]=[C:28]([CH:30]=[O:31])[O:27][N:26]=2)([OH:20])[CH3:22])=[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 866932353-(2-Hydroxybut-3-yn-2-yl)-1,2-oxazole-5-carbaldehyde

Product 1

HCID 866932329-Fluoro-10-(3-(5-formylisoxazol-3-yl)-3-hydroxybut-1-yn-1-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamideYield 10%

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 3-(2-hydroxybut-3-yn-2-yl)-1,2-oxazole-5-carbaldehyde to give the titled compound as a light yellow solid (14 mg, 10%).

Sources & evidence

ORD record
ord-9b1ce78079084e8db9e15d85d49868f6
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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