Diisopropylethylamine → (3aR,6aS)-tert-butyl 5-(6-(3-methylbenzamido)pyrazin-2-yl)hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate

HRID 240497Notes

Reaction equation

HRID 240497 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9](=[O:17])[C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[CH:11]=2)[CH:5]=[N:4][CH:3]=1.[CH2:18]1[C@@H:22]2[CH2:23][NH:24][CH2:25][C@@H:21]2[CH2:20][N:19]1[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27].C(N(CC)C(C)C)(C)C>CS(C)=O>[CH3:16][C:12]1[CH:11]=[C:10]([CH:15]=[CH:14][CH:13]=1)[C:9]([NH:8][C:6]1[N:7]=[C:2]([N:24]2[CH2:23][C@@H:22]3[CH2:18][N:19]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:20][C@@H:21]3[CH2:25]2)[CH:3]=[N:4][CH:5]=1)=[O:17]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1514452Cis-2-boc-hexahydropyrrolo[3,4-C]pyrroleHCID 86635811N-(6-chloropyrazin-2-yl)-3-methylbenzamide

Product 1

HCID 67265310(3aR,6aS)-tert-butyl 5-(6-(3-methylbenzamido)pyrazin-2-yl)hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
110 °C

Procedure

The product from Example 24A (130.5 mg, 0.53 mmol) was reacted with the product from Example 1C (149.6 mg, 0.70 mmol) and N,N-diisopropylethylamine (110 μL) in DMSO as described in Example 19A, except that the mixture was heated to 110° C. overnight, to afford the title compound. MS (DCI/NH3) m/z 424 (M+H)+.

Sources & evidence

ORD record
ord-e132583d500446debf87c4aa9d55f738
Source dataset
uspto-grants-2014_02
Patent number
US08648084B2

Reaction notes

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