P-Anisidine → 1-[(6-Aminopyridin-3-yl)methyl]-3-[(4-methoxyphenyl)amino]-4-phenyl-1H-pyrrole-2,5-dione

HRID 2113773Notes

Reaction equation

Cl[C:2]1[C:3](=[O:29])[N:4]([CH2:14][C:15]2[CH:16]=[CH:17][C:18]([NH:21]C(=O)OC(C)(C)C)=[N:19][CH:20]=2)[C:5](=[O:13])[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH3:30][O:31][C:32]1[CH:38]=[CH:37][C:35]([NH2:36])=[CH:34][CH:33]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[NH2:21][C:18]1[N:19]=[CH:20][C:15]([CH2:14][N:4]2[C:5](=[O:13])[C:6]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)=[C:2]([NH:36][C:35]3[CH:37]=[CH:38][C:32]([O:31][CH3:30])=[CH:33][CH:34]=3)[C:3]2=[O:29])=[CH:16][CH:17]=1

Participants

Conditions

Temperature: 150 °C

Procedure

To a solution of tert-butyl {5-[(3-chloro-2,5-dioxo-4-phenyl-2,5-dihydro-1H-pyrrol-1-yl)methyl]pyridin-2-yl}carbamate (0.86 mmol, 357 mg) in dry DMF (1.0 mL) was added 4-methoxyaniline (0.96 mmol, 118 mg) and anhydrous potassium carbonate (0.96 mmol, 133 mg) and the reaction mixture was subjected to microwave heating single node at 150° C. for 15 min. The reaction mixture was purified using HPLC (95% 0.1M ammonium acetate buffer:5% CH3CN→5% 0.1M ammonium acetate buffer: 95% CH3CN, 10 min., 25 mL/min.) to give 102 mg (29%) of the title compound. 1H NMR (400 MHz, CDCl3) δ 8.03 (s, 1H), 7.62 (dd, J=8.6 Hz, J=2.3 Hz, 1H), 7.21 (bs, 1H), 7.15-7.04 (m, 3H), 6.98-6.93 (m, 2H), 6.62-6.49 (m, 5H), 4.62 (s, 2H), 3.69 (s, 3H).

Workup

customThe reaction mixture was purified
customHPLC (95% 0.1M ammonium acetate buffer:5% CH3CN→5% 0.1M ammonium acetate buffer: 95% CH3CN, 10 min., 25 mL/min.)

Sources & evidence

ORD record: ord-ff2212d80e4e4c969bf8525de344358b
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07432288B2

Reaction notes

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