(R)-3-ethynyl-3-hydroxy-1-methylpyrrolidin-2-one → 9-fluoro-10-[2-[(3R)-3-hydroxy-1-methyl-2-oxo-pyrrolidin-3-yl]ethynyl]-3-(pyrrolidin-1-ylmethyl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2-carboxamide

HRID 575350

Reaction equation

HRID 575350 reaction equation
Br[C:2]1[C:3]([F:25])=[CH:4][C:5]2[O:11][CH2:10][CH2:9][N:8]3[C:12]([CH2:18][N:19]4[CH2:23][CH2:22][CH2:21][CH2:20]4)=[C:13]([C:15]([NH2:17])=[O:16])[N:14]=[C:7]3[C:6]=2[CH:24]=1.[C:26]([C@:28]1([OH:35])[CH2:32][CH2:31][N:30]([CH3:33])[C:29]1=[O:34])#[CH:27]>>[F:25][C:3]1[C:2]([C:27]#[C:26][C@:28]2([OH:35])[CH2:32][CH2:31][N:30]([CH3:33])[C:29]2=[O:34])=[CH:24][C:6]2[C:7]3[N:8]([C:12]([CH2:18][N:19]4[CH2:23][CH2:22][CH2:21][CH2:20]4)=[C:13]([C:15]([NH2:17])=[O:16])[N:14]=3)[CH2:9][CH2:10][O:11][C:5]=2[CH:4]=1

Participants

3

Reactant 2

HCID 86693296(R)-3-ethynyl-3-hydroxy-1-methylpyrrolidin-2-oneHCID 8669338510-Bromo-9-fluoro-3-(pyrrolidin-1-ylmethyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide

Product 1

HCID 866933879-fluoro-10-[2-[(3R)-3-hydroxy-1-methyl-2-oxo-pyrrolidin-3-yl]ethynyl]-3-(pyrrolidin-1-ylmethyl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2-carboxamideYield 3.3%

Procedure

10-bromo-9-fluoro-3-(pyrrolidin-1-ylmethyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide 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 3 mg (3.3%) of 9-fluoro-10-[2-[(3R)-3-hydroxy-1-methyl-2-oxo-pyrrolidin-3-yl]ethynyl]-3-(pyrrolidin-1-ylmethyl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2-carboxamide. M+1=468.2.

Sources & evidence

ORD record
ord-590d14645eb94c6c8aa79e716a9baf44
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Linked notes

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