Water → n-(4-{[2,5-Dihydro-1-(2-methoxyethyl)-2,5-dioxo-4-phenyl-1h-pyrrol-3-yl]amino}phenyl)-acetamide

HRID 2113752Notes

Reaction equation

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

Participants

Conditions

Temperature: 140 °C

Procedure

3-Chloro-1-(2-methoxyethyl)-4-phenyl-1H-pyrrole-2,5-dione (0.26 mmol, 70 mg) and 4-aminoacetanilide (0.53 mmol, 79 mg) was dissolved in dry CH3CN (2 mL) and the reaction mixture was subjected twice to microwave heating single node 140° 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 45 mg (45%) of the title compound. 1H NMR (400 MHz, CD3CN) δ 8.17 (bs, 1H), 7.78 (bs, 1H), 7.24-7.09 (m, 5H), 7.04-7.00 (m, 2H), 6.73-6.68 (m, 2H), 3.73 (t, J=5.7 Hz, 2H), 3.59 (t, J=5.7 Hz, 2H), 3.33 (s, 3H), 2.01 (s, 3H).

Workup

customthe reaction mixture was purified

Sources & evidence

ORD record: ord-94746a6fb18648259b4f475aae9e698f
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07432288B2

Reaction notes

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