m-Toluidine → (3aR,6aS)-tert-butyl 5-(5-(m-tolylcarbamoyl)pyridin-3-yl)hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate

HRID 240511Notes

Reaction equation

HRID 240511 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]2[CH2:13][N:14]([C:16]3[CH:17]=[N:18][CH:19]=[C:20]([CH:24]=3)[C:21](O)=[O:22])[CH2:15][C@H:10]2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[CH:27]=1>>[C:28]1([CH3:32])[CH:29]=[CH:30][CH:31]=[C:26]([NH:25][C:21]([C:20]2[CH:24]=[C:16]([N:14]3[CH2:15][C@@H:10]4[CH2:9][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])[CH2:12][C@@H:11]4[CH2:13]3)[CH:17]=[N:18][CH:19]=2)=[O:22])[CH:27]=1

Participants

3

Reactant 2

HCID 7934m-ToluidineHCID 672653675-((3aR,6aS)-5-(tert-butoxycarbonyl)hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)nicotinic Acid

Product 1

HCID 67265576(3aR,6aS)-tert-butyl 5-(5-(m-tolylcarbamoyl)pyridin-3-yl)hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate

Procedure

The product from Example 33B and m-toluidine were processed as described in Example 33C to provide the title compound. MS (APCI) m/z 423 (M+H)+.

Sources & evidence

ORD record
ord-43accc95daa647d8b58307d6333d2c42
Source dataset
uspto-grants-2014_02
Patent number
US08648084B2

Reaction notes

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