3-(5,6-Dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(5-(3-methylphenyl)-1H-indol-3-yl)pyrrole-2,5-dione → HCID 86608192, compound

HRID 388331Notes

Reaction equation

HRID 388331 reaction equation
[C:1]1([C:13]2[C:14](=[O:35])[NH:15][C:16](=[O:34])[C:17]=2[C:18]2[C:26]3[C:21](=[CH:22][CH:23]=[C:24]([C:27]4[CH:32]=[CH:31][CH:30]=[C:29]([CH3:33])[CH:28]=4)[CH:25]=3)[NH:20][CH:19]=2)[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH2:6][CH2:5][CH2:4][N:3]3[CH:2]=1>CO>[C:1]1([C@H:13]2[C@H:17]([C:18]3[C:26]4[C:21](=[CH:22][CH:23]=[C:24]([C:27]5[CH:32]=[CH:31][CH:30]=[C:29]([CH3:33])[CH:28]=5)[CH:25]=4)[NH:20][CH:19]=3)[C:16](=[O:34])[NH:15][C:14]2=[O:35])[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH2:6][CH2:5][CH2:4][N:3]3[CH:2]=1

Participants

3

Reactant 1

HCID 684946413-(5,6-Dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(5-(3-methylphenyl)-1H-indol-3-yl)pyrrole-2,5-dione

Product 1

HCID 86608192HCID 86608192, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-(5,6-Dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1yl)-4-(5-(3-methylphenyl)-1H-indol-3-yl)pyrrole-2,5-dione, prepared as in Example 34, was reduced with Mg in methanol as described in Example 2, Procedure C, to yield (±)-trans-3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1yl)-4-(5-(3-methylphenyl)-1H-indol-3-yl)pyrrolidine-2,5-dione. 1H NMR (CD3OD) δ: 1.98-2.18 (m, 2H), 2.34 (s, 3H), 2.85-3.00 (m, 2H), 3.90-3.98 (m, 1H), 3.98-4.09 (m, 1H), 4.35 (d, J=7.2 Hz, 1H), 4.64 (d, J=6.8 Hz, 1H), 6.88-6.99 (m, 2H), 7.00-7.10 (m, 3H), 7.13-7.26 (m, 5H), 7.36 (m, 2H).

Sources & evidence

ORD record
ord-c269306390334df4bdecad853ba77dfe
Source dataset
uspto-grants-2013_02
Patent number
US08377927B2

Reaction notes

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