P-Anisidine → 1-[4-(Dimethylamino)benzyl]-3-[(4-methoxyphenyl)amino]-4-phenyl-1H-pyrrole-2,5-dione

HRID 2113762Notes

Reaction equation

Cl[C:2]1[C:3](=[O:24])[N:4]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N:21]([CH3:23])[CH3:22])=[CH:17][CH:16]=2)[C:5](=[O:13])[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH3:25][O:26][C:27]1[CH:33]=[CH:32][C:30]([NH2:31])=[CH:29][CH:28]=1>CN(C=O)C>[CH3:22][N:21]([CH3:23])[C:18]1[CH:19]=[CH:20][C:15]([CH2:14][N:4]2[C:5](=[O:13])[C:6]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)=[C:2]([NH:31][C:30]3[CH:32]=[CH:33][C:27]([O:26][CH3:25])=[CH:28][CH:29]=3)[C:3]2=[O:24])=[CH:16][CH:17]=1

Participants

Conditions

Temperature: 150 °C

Procedure

3-Chloro-1-[4-(dimethylamino)benzyl]-4-phenyl-1H-pyrrole-2,5-dione (0.20 mmol, 68 mg) and 4-methoxyaniline (0.48 mmol, 59 mg) were dissolved in DMF (1 mL). The mixture was heated in a microwave reactor at 150° C. for five min. After cooling, the reaction mixture was purified by HPLC (95% 0.1M ammonium acetate buffer: 5% CH3CN→100% CH3CN) to give 11 mg (13%) of the title compound. 1H NMR (400 MHz, CDCl3) δ 7.38-7.34 (m, 2H), 7.15 (bs, 1H), 7.13-7.04 (m, 3H), 6.97 (m, 2H), 6.70 (d, 2H), 6.60-6.51 (m, 4H), 4.67 (s, 2H), 3.69 (s, 3H), 2.93 (s, 6H).

Workup

temperatureAfter cooling
customthe reaction mixture was purified by HPLC (95% 0.1M ammonium acetate buffer: 5% CH3CN→100% CH3CN)

Sources & evidence

ORD record: ord-7a3070f4e08c441989f8fa4782ad007a
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07432288B2

Reaction notes

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