(R)-3-ethynyl-3-hydroxy-1-methylpyrrolidin-2-one → HCID 86693407, compound

HRID 575365Notes

Reaction equation

HRID 575365 reaction equation
Br[C:2]1[C:22]([F:23])=[CH:21][C:5]2[O:6][CH2:7][C:8]([F:20])([F:19])[C:9]3[S:13][C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[N:11][C:10]=3[C:4]=2[CH:3]=1.[C:24]([C@:26]1([OH:33])[CH2:30][CH2:29][N:28]([CH3:31])[C:27]1=[O:32])#[CH:25]>>[F:19][C:8]1([F:20])[C:9]2[S:13][C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[N:11][C:10]=2[C:4]2[CH:3]=[C:2]([C:25]#[C:24][C@:26]3([OH:33])[CH2:30][CH2:29][N:28]([CH3:31])[C:27]3=[O:32])[C:22]([F:23])=[CH:21][C:5]=2[O:6][CH2:7]1

Participants

3

Reactant 2

HCID 86693296(R)-3-ethynyl-3-hydroxy-1-methylpyrrolidin-2-oneHCID 86693408HCID 86693408, compound

Product 1

HCID 86693407HCID 86693407, compound

Procedure

Ethyl 9-bromo-8-fluoro-4-oxo-4,5-dihydrobenzo[2,3]oxepino[4,5-d]thiazole-2-carboxylate was subjected to General Procedure P to afford 400 mg (95%) of ethyl 9-bromo-4,4,8-trifluoro-4,5-dihydrobenzo[2,3]oxepino[4,5-d]thiazole-2-carboxylate. Ethyl 9-bromo-4,4,8-trifluoro-4,5-dihydrobenzo[2,3]oxepino[4,5-d]thiazole-2-carboxylate was reacted with (3R)-3-ethynyl-3-hydroxy-1-methyl-pyrrolidin-2-one similarly to as described in General Procedure F with non-critical modifications to afford (R)-ethyl 4,4,8-trifluoro-9-((3-hydroxy-1-methyl-2-oxopyrrolidin-3-yl)ethynyl)-4,5-dihydrobenzo[2,3]oxepin o[4,5-d]thiazole-2-carboxylate. Crude (R)-ethyl 4,4,8-trifluoro-9-((3-hydroxy-1-methyl-2-oxopyrrolidin-3-yl)ethynyl)-4,5-dihydrobenzo[2,3]oxepin o[4,5-d]thiazole-2-carboxylate was subjected to General Procedure P to afford 190 mg (44.4%) of 4,4,8-trifluoro-9-[2-[(3R)-3-hydroxy-1-methyl-2-oxo-pyrrolidin-3-yl]ethynyl]-5H-[1]benzoxepino[5,4-d]thiazole-2-carboxamide. M+1=438.0.

Sources & evidence

ORD record
ord-8280c8b8b32b4f96bcfb971faf9d5cb4
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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