2-(5-Methylisoxazol-3-yl)but-3-yn-2-ol → (+/-)-9-Chloro-10-(3-hydroxy-3-(5-methylisoxazol-3-yl)but-1-yn-1-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide

HRID 575248Notes

Reaction equation

HRID 575248 reaction equation
Br[C:2]1[C:3]([Cl: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][C:21]1[O:25][N:24]=[C:23]([C:26]([OH:30])([C:28]#[CH:29])[CH3:27])[CH:22]=1>>[Cl:19][C:3]1[C:2]([C:29]#[C:28][C:26]([OH:30])([C:23]2[CH:22]=[C:21]([CH3:20])[O:25][N:24]=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 582217592-(5-Methylisoxazol-3-yl)but-3-yn-2-olHCID 8975549010-Bromo-9-chloro-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide

Product 1

HCID 89754598(+/-)-9-Chloro-10-(3-hydroxy-3-(5-methylisoxazol-3-yl)but-1-yn-1-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamideYield 32%

Procedure

Similar to as describe in General Procedure G, 10-bromo-9-chloro-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide was reacted with racemic 2-(5-methyl-1,2-oxazol-3-yl)but-3-yn-2-ol to give the titled compound as a yellow solid (40 mg, 32%).

Sources & evidence

ORD record
ord-27724e76e6a9483b8b77ae2fb24e6483
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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