Water → 3-[(4-Morpholin-4-ylphenyl)amino]-4-phenyl-1-(pyridin-3-ylmethyl)-1H-pyrrole-2,5-dione

HRID 2113756Notes

Reaction equation

[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.Cl[C:15]1[C:16](=[O:34])[N:17]([CH2:27][C:28]2[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=2)[C:18](=[O:26])[C:19]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O>CC#N>[N:4]1([C:7]2[CH:13]=[CH:12][C:10]([NH:11][C:15]3[C:16](=[O:34])[N:17]([CH2:27][C:28]4[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=4)[C:18](=[O:26])[C:19]=3[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[CH:9][CH:8]=2)[CH2:3][CH2:2][O:1][CH2:6][CH2:5]1

Participants

Conditions

Temperature: 130 °C

Procedure

4-Morpholinoaniline (0.94 mmol, 178 mg) dissolved in dry CH3CN (2 mL) was added to crude 3-chloro-4-phenyl-1-(pyridin-3-ylmethyl)-1H-pyrrole-2,5-dione (0.47 mmol, 140 mg) and the reaction mixture was subjected to microwave heating single node 130° C. for 10 min. 0.3 mL water was added and the reaction mixture was purified using HPLC (57% 0.1M ammonium acetate buffer: 43% CH3CN→100% CH3CN, 20 mL/min) to give 56 mg (27%) of the title compound. 1H NMR (400 MHz, CD3CN) δ 8.63 (d, 1H), 8.51 (dd, 1H), 7.81-7.73 (m, 1H), 7.36-7.31 (m, 1H), 7.16-7.11 (m,1H), 7.10-7.04 (m, 2H), 6.99-6.93 (m, 2H), 6.69-6.64 (m, 2H), 6.59-6.53 (m, 2H), 4.75 (s, 2H), 3.74 (t, J=4.8 Hz, 4H), 2.97 (t, J=4.8 Hz, 4H).

Workup

customthe reaction mixture was purified

Sources & evidence

ORD record: ord-41681ea0e800449885ba73028c4a9831
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07432288B2

Reaction notes

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