Water → 3-Phenyl-1-(pyridin-3-ylmethyl)-4-{[4-(trifluoromethoxy)phenyl]amino}-1H-pyrrole-2,5-dione

HRID 2113758Notes

Reaction equation

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

Participants

Conditions

Temperature: 140 °C

Procedure

4-(Trifluoromethoxy)aniline (0.94 mmol, 177 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 sequentially subjected to microwave heating single node 140° C. for 20 min, 140° C. for 120 min, and 140° C. for 120 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 92 mg (45%) of the title compound. 1H NMR (400 MHz, CD3CN) δ 8.63 (d, 1H), 8.52 (dd, 1H), 7.95 (bs, 1H), 7.80-7.74 (m, 1H), 7.37-7.32 (m, 1H), 7.19-7.08 (m, 3H), 7.01-6.95 (m, 2H), 6.94-6.88 (m, 2H), 6.84-7.78 (m, 2H), 4.77 (s, 2H).

Workup

customthe reaction mixture was purified

Sources & evidence

ORD record: ord-cd63f98d93774f71bf7ae97bd9aeb3ae
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07432288B2

Reaction notes

Loading…