9-Bromo-4,5-dihydro-[1]benzoxepino[5,4-d]thiazole-2-carboxamide → (+/-)-9-((3-Hydroxy-1-methyl-2-oxopyrrolidin-3-yl)ethynyl)-4,5-dihydrobenzo[2,3]oxepino[4,5-d]thiazole-2-carboxamide

HRID 575190Notes

Reaction equation

HRID 575190 reaction equation
Br[C:2]1[CH:18]=[CH:17][C:5]2[O:6][CH2:7][CH2:8][C:9]3[S:13][C:12]([C:14]([NH2:16])=[O:15])=[N:11][C:10]=3[C:4]=2[CH:3]=1.[C:19]([C:21]1([OH:28])[CH2:25][CH2:24][N:23]([CH3:26])[C:22]1=[O:27])#[CH:20]>>[OH:28][C:21]1([C:19]#[C:20][C:2]2[CH:18]=[CH:17][C:5]3[O:6][CH2:7][CH2:8][C:9]4[S:13][C:12]([C:14]([NH2:16])=[O:15])=[N:11][C:10]=4[C:4]=3[CH:3]=2)[CH2:25][CH2:24][N:23]([CH3:26])[C:22]1=[O:27]

Participants

3

Reactant 2

HCID 582039029-Bromo-4,5-dihydro-[1]benzoxepino[5,4-d]thiazole-2-carboxamideHCID 58221634HCID 58221634, compound

Product 1

HCID 71666344(+/-)-9-((3-Hydroxy-1-methyl-2-oxopyrrolidin-3-yl)ethynyl)-4,5-dihydrobenzo[2,3]oxepino[4,5-d]thiazole-2-carboxamideYield 48%

Procedure

Similar to as described in General Procedure G, 9-bromo-4,5-dihydrobenzo[2,3]oxepino[4,5-d]thiazole-2-carboxamide) was reacted with 3-ethynyl-3-hydroxy-1-methylpyrrolidin-2-one (WO2009/158011 A1) to give the titled compound as a brown solid (56.1 mg, 48%).

Sources & evidence

ORD record
ord-f80940854ce7429390c9731147511e5c
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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