HCID 25165712, compound → HCID 25110676, compound

HRID 1873673Notes

Reaction equation

HRID 1873673 reaction equation
[C:1]1([C@@H:13]2[C:17](=S)[NH:16][C:15](=[O:19])[C@H:14]2[C:20]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[NH:22][CH:21]=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.[C:29]1([C@H:41]2[C@H:45]([C:46]3[C:54]4[C:49](=[CH:50][CH:51]=[CH:52][CH:53]=4)[NH:48][CH:47]=3)[C:44](=S)[NH:43][C:42]2=[O:56])[C:39]2=[C:40]3[C:35](=[CH:36][CH:37]=[CH:38]2)[CH2:34][CH2:33][CH2:32][N:31]3[CH:30]=1>CO.[Ni]>[C:1]1([C@@H:13]2[CH2:17][NH:16][C:15](=[O:19])[C@H:14]2[C:20]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[NH:22][CH:21]=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.[C:29]1([C@H:41]2[C@H:45]([C:46]3[C:54]4[C:49](=[CH:50][CH:51]=[CH:52][CH:53]=4)[NH:48][CH:47]=3)[CH2:44][NH:43][C:42]2=[O:56])[C:39]2=[C:40]3[C:35](=[CH:36][CH:37]=[CH:38]2)[CH2:34][CH2:33][CH2:32][N:31]3[CH:30]=1

Participants

6

Reactant 2

HCID 25165712HCID 25165712, compoundHCID 25165713HCID 25165713, compound

Product 2

HCID 25110676HCID 25110676, compoundYield 34%HCID 25165710HCID 25165710, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A solution of (3R,4R)-4-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-3-(1H-indol-3-yl)-5-thioxo-pyrrolidin-2-one and (3R,4R)-3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)-5-thioxo-pyrrolidin-2-one (0.070 g, 0.181 mmol) in methanol (15 mL) was treated with excess Raney nickel. The mixture was stirred at room temperature for 15 min. The reaction mixture was filtered over a pad of celite under N2 and the solvent removed under reduced pressure. The residue was purified by flash chromatography (ethyl acetate:methanol; 98:2) giving a mixture (1/1) of regio isomers (3R,4R)-4-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-3-(1H-indol-3-yl)-pyrrolidin-2-one and (3R,4R)-3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)-pyrrolidin-2-one (22 mg, 34%). 1H NMR (400 MHz, DMSO-d6) δ: 10.84 (d, J=13.6 Hz, 1H), 7.91 (brs, 1H), 7.46 (dd, J=7.7 and 13.6 Hz, 1H), 7.30-7.16 (m, 4H), 7.02 (m, 1H), 6.90 (m, 1H), 6.84-6.78 (m, 3H), 4.04 (brs, 2H), 4.0 (m, 1H), 3.72 (m, 1H), 3.35 (brs, 2H), 2.86 (brm, 2H), 2.07 (brm, 2H). LCMS: 356 [M+H].

Workup

  1. filtrationThe reaction mixture was filtered over a pad of celite under N2
  2. customthe solvent removed under reduced pressure
  3. customThe residue was purified by flash chromatography (ethyl acetate:methanol; 98:2)

Sources & evidence

ORD record
ord-f81f3b6658ee46a5807b643ce8bb09a8
Source dataset
uspto-grants-2012_11
Patent number
US08304425B2

Reaction notes

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