rac-tert-butyl (3aR,6aR)-octahydropyrrolo(3,4-b)pyrrole-5-carboxylate → (3aS,6aS)-tert-butyl 1-(5-(3,5-difluorophenylcarbamoyl)pyridin-3-yl)hexahydropyrrolo[3,2-c]pyrrole-5(1H)-carboxylate

HRID 240527Notes

Reaction equation

HRID 240527 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:18]=1)[C:7]([NH:9][C:10]1[CH:15]=[C:14]([F:16])[CH:13]=[C:12]([F:17])[CH:11]=1)=[O:8].[NH:19]1[CH2:23][CH2:22][C@H:21]2[CH2:24][N:25]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:26][C@@H:20]12>>[F:17][C:12]1[CH:11]=[C:10]([NH:9][C:7]([C:6]2[CH:18]=[C:2]([N:19]3[C@H:20]4[C@H:21]([CH2:24][N:25]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:26]4)[CH2:22][CH2:23]3)[CH:3]=[N:4][CH:5]=2)=[O:8])[CH:15]=[C:14]([F:16])[CH:13]=1

Participants

3

Reactant 2

HCID 16227750rac-tert-butyl (3aR,6aR)-octahydropyrrolo(3,4-b)pyrrole-5-carboxylateHCID 416011495-bromo-N-(3,5-difluorophenyl)nicotinamide

Product 1

HCID 67265701(3aS,6aS)-tert-butyl 1-(5-(3,5-difluorophenylcarbamoyl)pyridin-3-yl)hexahydropyrrolo[3,2-c]pyrrole-5(1H)-carboxylate

Procedure

The product from Example 53A and (3aS,6aS)-tert-butyl hexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxylate (prepared as described in WO2001081347) were processed as described in Example 53B to provide the title compound. MS (APCI) m/z=445 (M+H)+.

Sources & evidence

ORD record
ord-9d83397f0d744df38e4a553f848171e8
Source dataset
uspto-grants-2014_02
Patent number
US08648084B2

Reaction notes

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