3-Ethynyl-3-hydroxy-1-methylpiperidin-2-one → (+/-)-8-Fluoro-9-((3-hydroxy-1-methyl-2-oxopiperidin-3-yl)ethynyl)-4,5-dihydrobenzo[2,3]oxepino[4,5-d]thiazole-2-carboxamide

HRID 575191Notes

Reaction equation

HRID 575191 reaction equation
Br[C:2]1[C:18]([F:19])=[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:20]([C:22]1([OH:30])[CH2:27][CH2:26][CH2:25][N:24]([CH3:28])[C:23]1=[O:29])#[CH:21]>>[F:19][C:18]1[C:2]([C:21]#[C:20][C:22]2([OH:30])[CH2:27][CH2:26][CH2:25][N:24]([CH3:28])[C:23]2=[O:29])=[CH:3][C:4]2[C:10]3[N:11]=[C:12]([C:14]([NH2:16])=[O:15])[S:13][C:9]=3[CH2:8][CH2:7][O:6][C:5]=2[CH:17]=1

Participants

3

Reactant 2

HCID 866695763-Ethynyl-3-hydroxy-1-methylpiperidin-2-oneHCID 866930599-Bromo-8-fluoro-4,5-dihydro-[1]benzoxepino[5,4-d]thiazole-2-carboxamide

Product 1

HCID 86693199(+/-)-8-Fluoro-9-((3-hydroxy-1-methyl-2-oxopiperidin-3-yl)ethynyl)-4,5-dihydrobenzo[2,3]oxepino[4,5-d]thiazole-2-carboxamideYield 16%

Procedure

Similar to as described in General Procedure G, 9-bromo-8-fluoro-4,5-dihydrobenzo[2,3]oxepino[4,5-d]thiazole-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, 16%).

Sources & evidence

ORD record
ord-9d0d36dd2a9b48098c3522378d0cb4aa
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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