(R)-3-ethynyl-3-hydroxy-1-methylpyrrolidin-2-one → HCID 86693403, compound

HRID 575363Notes

Reaction equation

HRID 575363 reaction equation
Br[C:2]1[C:19]([F:20])=[CH:18][C:5]2[O:6][CH2:7][CH2:8][C:9]3[CH:13]=[C:12]([C:14]([O:16][CH3:17])=[O:15])[S:11][C:10]=3[C:4]=2[CH:3]=1.[C:21]([C@:23]1([OH:30])[CH2:27][CH2:26][N:25]([CH3:28])[C:24]1=[O:29])#[CH:22]>>[F:20][C:19]1[C:2]([C:22]#[C:21][C@:23]2([OH:30])[CH2:27][CH2:26][N:25]([CH3:28])[C:24]2=[O:29])=[CH:3][C:4]2[C:10]3[S:11][C:12]([C:14]([O:16][CH3:17])=[O:15])=[CH:13][C:9]=3[CH2:8][CH2:7][O:6][C:5]=2[CH:18]=1

Participants

3

Reactant 2

HCID 86693296(R)-3-ethynyl-3-hydroxy-1-methylpyrrolidin-2-oneHCID 86693404HCID 86693404, compound

Product 1

HCID 86693403HCID 86693403, compound

Procedure

Methyl 9-bromo-8-fluoro-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-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)-methyl 8-fluoro-9-((3-hydroxy-1-methyl-2-oxopyrrolidin-3-yl)ethynyl)-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxylate. Crude (R)-methyl 8-fluoro-9-((3-hydroxy-1-methyl-2-oxopyrrolidin-3-yl)ethynyl)-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxylate was to General Procedure M subjected to afford 26 mg (21%) of 8-fluoro-9-[2-[(3R)-3-hydroxy-1-methyl-2-oxo-pyrrolidin-3-yl]ethynyl]-4,5-dihydrothieno[3,2-d][1]benzoxepine-2-carboxamide.

Sources & evidence

ORD record
ord-cb823a3f11364eb880461ea9d48a952c
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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