(R)-3-ethynyl-3-hydroxy-1-methylpyrrolidin-2-one → HCID 86693397, compound

HRID 575358Notes

Reaction equation

HRID 575358 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:11][CH2:10][CH2:9][N:8]3[C:12]([C:18]([NH:20][CH:21]([CH3:23])[CH3:22])=[O:19])=[C:13]([C:15]([NH2:17])=[O:16])[N:14]=[C:7]3[C:6]=2[CH:24]=1.[C:25]([C@:27]1([OH:34])[CH2:31][CH2:30][N:29]([CH3:32])[C:28]1=[O:33])#[CH:26]>>[OH:34][C@@:27]1([C:25]#[C:26][C:2]2[CH:3]=[CH:4][C:5]3[O:11][CH2:10][CH2:9][N:8]4[C:12]([C:18]([NH:20][CH:21]([CH3:23])[CH3:22])=[O:19])=[C:13]([C:15]([NH2:17])=[O:16])[N:14]=[C:7]4[C:6]=3[CH:24]=2)[CH2:31][CH2:30][N:29]([CH3:32])[C:28]1=[O:33]

Participants

3

Reactant 2

HCID 86693296(R)-3-ethynyl-3-hydroxy-1-methylpyrrolidin-2-oneHCID 86693398HCID 86693398, compound

Product 1

HCID 86693397HCID 86693397, compoundYield 12.2%

Procedure

10-bromo-2-carbamoyl-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-3-carboxyl is acid was reacted with 2-aminopropane similarly to as described in example 2 with non-critical modifications to afford 112 mg (67%) 10-bromo-N3-isopropyl-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2,3-dicarboxamide. 10-bromo-N3-isopropyl-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2,3-dicarboxamide 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 16 mg (12.2%) 10-[2-[(3R)-3-hydroxy-1-methyl-2-oxo-pyrrolidin-3-yl]ethynyl]-N3-isopropyl-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2,3-dicarboxamide.

Sources & evidence

ORD record
ord-7225bb3c988d442daeeca845329fb3f8
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

Loading…