1-(5-Fluoro-2-methylphenyl)propan-2-amine → 2-(4-((1-(5-Fluoro-2-methylphenyl)propan-2-yl)amino)-2-oxo-1,2-dihydropyridin-3-yl)-6-isopropylimidazo[4,5-f]isoindole-5,7(1H,6H)-dione

HRID 69369Notes

Reaction equation

HRID 69369 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:12])=[C:6]([CH2:8][CH:9]([NH2:11])[CH3:10])[CH:7]=1.Cl[C:14]1[CH:19]=[CH:18][NH:17][C:16](=[O:20])[C:15]=1[C:21]1[NH:37][C:24]2=[CH:25][C:26]3[C:27](=[O:36])[N:28]([CH:33]([CH3:35])[CH3:34])[C:29](=[O:32])[C:30]=3[CH:31]=[C:23]2[N:22]=1>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:12])=[C:6]([CH2:8][CH:9]([NH:11][C:14]2[CH:19]=[CH:18][NH:17][C:16](=[O:20])[C:15]=2[C:21]2[NH:22][C:23]3=[CH:31][C:30]4[C:29](=[O:32])[N:28]([CH:33]([CH3:35])[CH3:34])[C:27](=[O:36])[C:26]=4[CH:25]=[C:24]3[N:37]=2)[CH3:10])[CH:7]=1

Participants

3

Reactant 2

HCID 552546731-(5-Fluoro-2-methylphenyl)propan-2-amineHCID 1363406532-(4-Chloro-2-oxo-1,2-dihydropyridin-3-yl)-6-isopropylimidazo[4,5-f]isoindole-5,7(1H,6H)-dione

Product 1

HCID 1363406552-(4-((1-(5-Fluoro-2-methylphenyl)propan-2-yl)amino)-2-oxo-1,2-dihydropyridin-3-yl)-6-isopropylimidazo[4,5-f]isoindole-5,7(1H,6H)-dioneYield 127.3%

Procedure

Racemic 1-(5-fluoro-2-methylphenyl)propan-2-amine (0.13 g) and 2-(4-chloro-2-oxo-1,2-dihydropyridin-3-yl)-6-isopropylimidazo[4,5-f]isoindole-5,7(1H,6H)-dione (0.2965 mmol) were submitted to general procedure A to give 0.184 g the title compound. 1H NMR (500 MHz, CDCl3) δ 13.07 (s, 1H), 11.14 (d, 1H), 10.09 (s, 1H), 8.07 (s, 1H), 7.87 (s, 1H), 7.16-7.14 (m, 1H), 7.10-7.06 (m, 1H), 6.97 (d, 1H), 6.89-6.77 (m, 2H), 5.95 (d, 1H), 4.93 (br s, 1H), 4.57 (br s, 1H), 4.02 (br s, 1H), 3.14-3.04 (m, 1H), 3.04-2.94 (m, 1H), 2.36 (s, 3H), 1.54 (d, 6H), 1.48 (d, 3H). APCI MS: m/z 485.9 (M+1).

Sources & evidence

ORD record
ord-cacb87a71ab64d0bb6d42a69f0bd9de8
Source dataset
uspto-grants-2014_09
Patent number
US08822500B2

Reaction notes

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