Tert-butyl octahydropyrrolo(3,4-c)pyrrole-2-carboxylate → HCID 46189493, compound

HRID 1963030Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[C:11]3[CH2:13][N:14]([C:17]4[CH:18]=[N:19][C:20](F)=[CH:21][CH:22]=4)[C:15](=[O:16])[C:10]3=[N:9]2)=[CH:4][CH:3]=1.[CH2:24]1[CH:28]2[CH2:29][NH:30][CH2:31][CH:27]2[CH2:26][N:25]1[C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33]>CS(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[C:11]3[CH2:13][N:14]([C:17]4[CH:22]=[CH:21][C:20]([N:30]5[CH2:29][CH:28]6[CH2:24][N:25]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:26][CH:27]6[CH2:31]5)=[N:19][CH:18]=4)[C:15](=[O:16])[C:10]3=[N:9]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 140 °C

Procedure

To a mixture of Example 34A (20 mg, 0.061 mmol) in DMSO (0.8 mL) was added tert-butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate (63 mg, 0.297 mmol). The resulting mixture was irradiated in microwave reactor at 140° C. for 30 min. The sealed tube was heated at 140° C. for 3 h and allowed to cool down to room temperature. The reaction mixture was subjected to filtration. The solid collected was further washed with MeOH (5 mL) and dried under vacuum to give product (19.5 mg) as light yellow solid. 1H NMR (CDCl3, 400 MHz) δ 1.60 (s, 9H), 2.90-3.05 (m, 2H), 3.20-3.50 (m, 4H), 3.60-3.80 (m, 4H), 4.77 (s, 2H), 6.42 (d, J=8.8 Hz, 1H), 7.43-7.50 (m, 2H), 7.72-7.76 (m, 2H), 7.89 (s, 1H), 8.07 (dd, J=8.8, 2.7 Hz, 1H), 8.28 (d, J=2.7 Hz, 1H). LCMS, [M+H]+=521.4.

Workup

customThe resulting mixture was irradiated in microwave reactor at 140° C. for 30 min
temperatureto cool down to room temperature
filtrationThe reaction mixture was subjected to filtration
customThe solid collected
washwas further washed with MeOH (5 mL)
customdried under vacuum

Sources & evidence

ORD record: ord-799cf80ecf584daeb177179983543646
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08415386B2

Reaction notes

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