10-Bromo-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide → (+/-)-10-((3-Hydroxy-1-methyl-2-oxopiperidin-3-yl)ethynyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide

HRID 575195Notes

Reaction equation

HRID 575195 reaction equation
Br[C:2]1[CH:3]=[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.[C:19]([C:21]1([OH:29])[CH2:26][CH2:25][CH2:24][N:23]([CH3:27])[C:22]1=[O:28])#[CH:20]>>[OH:29][C:21]1([C:19]#[C:20][C:2]2[CH:3]=[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)[CH2:26][CH2:25][CH2:24][N:23]([CH3:27])[C:22]1=[O:28]

Participants

3

Reactant 2

HCID 6831288310-Bromo-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamideHCID 866695763-Ethynyl-3-hydroxy-1-methylpiperidin-2-one

Product 1

HCID 86693201(+/-)-10-((3-Hydroxy-1-methyl-2-oxopiperidin-3-yl)ethynyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamideYield 17%

Procedure

Similar to as described in General Procedure G, 10-bromo-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide was reacted with 3-ethynyl-3-hydroxy-1-methylpiperidin-2-one (US2012/214762A1) to give the titled compound as a white solid (20 mg, 17%).

Sources & evidence

ORD record
ord-84f61f83dd704630904f31bb4814ebd4
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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