5-bromo-N-(2-methylbenzyl)nicotinamide → (3aS,6aS)-tert-butyl 1-(5-(2-methylbenzylcarbamoyl)pyridin-3-yl)hexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxylate

HRID 1685501Notes

Reaction equation

HRID 1685501 reaction equation
[NH:1]1[CH2:5][CH2:4][C@H:3]2[CH2:6][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:8][C@@H:2]12.Br[C:17]1[CH:18]=[N:19][CH:20]=[C:21]([CH:33]=1)[C:22]([NH:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[CH3:32])=[O:23]>>[CH3:32][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[CH2:25][NH:24][C:22]([C:21]1[CH:33]=[C:17]([N:1]2[CH2:5][CH2:4][C@H:3]3[CH2:6][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:8][C@@H:2]23)[CH:18]=[N:19][CH:20]=1)=[O:23]

Participants

3

Reactant 2

HCID 91046105-bromo-N-(2-methylbenzyl)nicotinamideHCID 16227750rac-tert-butyl (3aR,6aR)-octahydropyrrolo(3,4-b)pyrrole-5-carboxylate

Product 1

HCID 67265849(3aS,6aS)-tert-butyl 1-(5-(2-methylbenzylcarbamoyl)pyridin-3-yl)hexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxylate

Procedure

Prepared from (3aS,6aS)-tert-butyl hexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxylate (prepared as described in WO2001081347) and the product from Example 31A using the procedure as described in Example 31B. MS (APCI) m/z 437 (M+H)+.

Sources & evidence

ORD record
ord-d6744f7d35d34305ab61edb8a0ae897b
Source dataset
uspto-grants-2012_04
Patent number
US08148408B2

Reaction notes

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