2-(2-Chloro-4-fluorophenyl)acetamide → (+/-)-Trans-3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1yl)-4-(4-trifluoromethoxyphenyl)pyrrolidine-2,5-dione

HRID 63563Notes

Reaction equation

HRID 63563 reaction equation
Cl[C:2]1[CH:7]=[C:6](F)[CH:5]=[CH:4][C:3]=1[CH2:9][C:10]([NH2:12])=O.[F:13][C:14]([F:27])([F:26])[O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23]([NH2:25])=[O:24])=[CH:18][CH:17]=1>>[C:9]1([C@H:17]2[C@H:22]([C:19]3[CH:18]=[CH:17][C:16]([O:15][C:14]([F:26])([F:27])[F:13])=[CH:21][CH:20]=3)[C:23](=[O:24])[NH:25][C:16]2=[O:15])[C:3]2=[C:4]3[C:5](=[CH:6][CH:7]=[CH:2]2)[CH2:20][CH2:19][CH2:18][N:12]3[CH:10]=1

Participants

3

Reactant 2

HCID 27737162-(2-Chloro-4-fluorophenyl)acetamideHCID 187035932-[4-(Trifluoromethoxy)phenyl]acetamide

Product 1

HCID 86608196(+/-)-Trans-3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1yl)-4-(4-trifluoromethoxyphenyl)pyrrolidine-2,5-dione

Procedure

(±)-Trans-3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1yl)-4-(4-trifluoromethoxyphenyl) pyrrolidine-2,5-dione was prepared according to Example 40 replacing 2-chloro-4-fluorophenylacetamide with 4-trifluoromethoxyphenylacetamide. Yield 67.8 mg, 16.4%. 1H NMR (DMSO-d6) 400 MHz δ: 11.56 (s, 1H), 7.52 (d, 2H, J=8.4 Hz), 7.35 (s, 1H), 7.33 (d, 2H, J=8.0 Hz), 7.15 (d, 1H, J=7.2 Hz), 6.86 (m, 2H), 4.58 (d, 1H, J=8.0 Hz), 4.45 (d, 1H, J=8.0 Hz), 4.10 (t, 2H, J=6.0 Hz), 2.90 (t, 2H, J=6.0), 2.10 (t, 2H, J=5.6).

Sources & evidence

ORD record
ord-0bf8677c727c428cbaa68ecd635f7b99
Source dataset
uspto-grants-2016_09
Patent number
US09447088B2

Reaction notes

Loading…