Indole-3-acetamide → 3-(5,6-Dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)-1H-pyrrole-2,5-dione

HRID 709007Notes

Reaction equation

HRID 709007 reaction equation
[C:1]1([C@H:13]2[C@@H:17]([C:18]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[NH:20][CH:19]=3)[C:16](=[O:27])[NH:15][C:14]2=[O:28])[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.N1C2C(=CC=CC=2)CCC1.N1C2C(=CC=CC=2)C(CC(N)=O)=C1.COC(=O)C=O>>[C:1]1([C:13]2[C:14](=[O:28])[NH:15][C:16](=[O:27])[C:17]=2[C:18]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][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

Participants

5

Reactant 4

HCID 397Indole-3-acetamide2×HCID 694601,2,3,4-Tetrahydroquinoline2×HCID 70205Acetic acid, 2-oxo-, methyl ester2×HCID 11717641(+)-cis-3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4(1H-indol-3-yl)pyrrolidine-2,5-dione

Product 1

HCID 99692093-(5,6-Dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)-1H-pyrrole-2,5-dione

Procedure

Compounds of the invention can be prepared according to the synthetic schemes described in WO 2006/086484, U.S. Pat. No. 7,713,969, and US 20100221251, each of which is incorporated by reference in its entirety for all purposes. Briefly, the preparation of (±)-cis-3-(5,6-dihydro-4H-pyrrolo [3,2,1-ij] quinolin-1-yl)-4-(1H-indol-3-yl) pyrrolidine-2,5-dione is prepared as a mixture beginning with the starting materials 1,2,3,4-tetrahydroquinoline and indole-3-acetamide. The 1,2,3,4-tetrahydroquinoline is converted into 5,6-dihydro-4H-pyrrolo [3,2,1-ij] quinolin-1-yl) oxoacetic acid methyl ester as described in Example 1, steps 1-5 of WO2006/086484, U.S. Pat. No. 7,713,969, and US 20100221251. The 5,6-dihydro-4H-pyrrolo [3,2,1-ij] quinolin-1-yl) oxoacetic acid methyl ester is reacted with indole-3-acetamide as described in Example 1, step 6 of WO2006/086484, U.S. Pat. No. 7,713,969, and US 20100221251, to yield 3-(5,6-dihydro-4H-pyrrolo [3,2,1-ij] quinolin-1-yl)-4-(1H-indol-3-yl) pyrrole-2,5-dione. The mixture of (±)-cis-3-(5,6-dihydro-4H-pyrrolo [3,2,1-ij] quinolin-1-yl)-4-(1H-indol-3-yl) pyrrolidine-2,5-dione is then prepared by catalytic hydrogenation as described in Example 2 using Procedure B of WO2006/086484, U.S. Pat. No. 7,713,969, and US 20100221251.

Workup

  1. customCompounds of the invention can be prepared
  2. customis prepared as a mixture

Sources & evidence

ORD record
ord-7ebbbea6fb104b5b85168e9f23180d8b
Source dataset
uspto-grants-2015_11
Patent number
US09180099B2

Reaction notes

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