Water → HCID 11476107, compound

HRID 2113757Notes

Reaction equation

[NH2:1][C:2]1[CH:13]=[CH:12][C:5]2[O:6][C:7]([C:9](=[O:11])[CH3:10])=[CH:8][C:4]=2[CH:3]=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>[C:9]([C:7]1[O:6][C:5]2[CH:12]=[CH:13][C:2]([NH:1][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:3][C:4]=2[CH:8]=1)(=[O:11])[CH3:10]

Participants

Conditions

Temperature: 130 °C

Procedure

1-(5-Aminobenzo[b]furan-2-yl)ethan-1-one (0.94 mmol, 164 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 15 mg (7%) of the title compound. 1H NMR (400 MHz, CD3CN) δ 8.64 (d, 1H), 8.52 (dd, 1H), 8.01 (bs, 1H), 7.80-7.75 (m, 1H), 7.35 (dd, 1H), 7.31-7.23 (m, 2H), 7.08-6.93 (m, 7H), 4.77 (s, 2H), 2.50 (s, 3H).

Workup

customthe reaction mixture was purified

Sources & evidence

ORD record: ord-be00a94617214cc3a7f839755b1cda66
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07432288B2

Reaction notes

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