P-Anisidine → HCID 11224515, compound

HRID 2113766Notes

Reaction equation

Cl[C:2]1[C:3](=[O:25])[N:4]([CH2:14][C:15]2[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[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.[CH3:26][O:27][C:28]1[CH:34]=[CH:33][C:31]([NH2:32])=[CH:30][CH:29]=1.C(N(CC)CC)C>CN(C=O)C>[CH3:26][O:27][C:28]1[CH:34]=[CH:33][C:31]([NH:32][C:2]2[C:3](=[O:25])[N:4]([CH2:14][C:15]3[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:16]=3)[C:5](=[O:13])[C:6]=2[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:30][CH:29]=1

Participants

Conditions

Temperature: 150 °C

Procedure

Methyl 4-[(3-chloro-2,5-dioxo-4-phenyl-2,5-dihydro-1H-pyrrol-1-yl)methyl]benzoate (0.24 mmol, 85 mg), 4-methoxyaniline (0.26 mmol, 33 mg) and triethylamine (0.29 mmol, 29 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 32 mg (30%) of the title compound. 1H NMR (400 MHz, CDCl3) δ 8.03-7.99 (m, 2H), 7.52-7.46 (m, 2H), 7.21 (bs, 1H), 7.16-7.05 (m, 3H), 7.01-6.95 (m, 2H), 6.62-6.52 (m, 4H), 4.81 (s, 2), 3.90 (s, 3H), 3.69 (s, 3H).

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-5ac32ba7d7e242de9a0bf9be52f392a1
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07432288B2

Reaction notes

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