Acetonitrile → 1-[(6-Aminopyridin-3-yl)methyl]-3-[(4-morpholin-4-ylphenyl)amino]-4-phenyl-1H-pyrrole-2,5-dione

HRID 2113775Notes

Reaction equation

HRID 2113775 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)[O:23][C:24]([CH3:27])(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.[O:30]1[CH2:35][CH2:34][N:33]([C:36]2[CH:42]=[CH:41][C:39]([NH2:40])=[CH:38][CH:37]=2)[CH2:32][CH2:31]1.CC#N>CN(C=O)C>[C:24]([O-:30])(=[O:23])[CH3:27].[NH4+:4].[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:40][C:39]3[CH:41]=[CH:42][C:36]([N:33]4[CH2:32][CH2:31][O:30][CH2:35][CH2:34]4)=[CH:37][CH:38]=3)[C:3]2=[O:29])=[CH:16][CH:17]=1

Participants

6

Reactant 3

HCID 6342Acetonitrile2×HCID 75655Benzenamine, 4-(4-morpholinyl)-HCID 86607353tert-Butyl {5-[(3-chloro-2,5-dioxo-4-phenyl-2,5-dihydro-1H-pyrrol-1-yl)methyl]pyridin-2-yl}carbamate

Product 2

HCID 517165Ammonium AcetateYield 60%HCID 112940051-[(6-Aminopyridin-3-yl)methyl]-3-[(4-morpholin-4-ylphenyl)amino]-4-phenyl-1H-pyrrole-2,5-dioneYield 83.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of tert-Butyl {5-[(3-chloro-2,5-dioxo-4-phenyl-2,5-dihydro-1H-pyrrol-1-yl)methyl]pyridin-2-yl}carbamate (0.85 g, 2.06 mmol ) and 4-morpholinoaniline (0.73 g, 4.12 mmol) in DMF (4 mL) was heated in a microwave reactor at 150° C. for 10 min. Preparative HPLC (C18, 50×250 mm, 60% 0.1M ammonium acetate buffer: 40% CH3CN→100% CH3CN) gave 0.39 g (42%) of the title compound. 1H NMR (400 MHz, CDCl3) δ 8.14 (bs, 1H), 7.55 (dd, J=8, 2 Hz, 1H), 7.28-7.23 (br, 1H), 7.13-7.04 (m, 3H), 6.95 (dd, J=8, 2 Hz, 2H), 6.57-6.51 (m, 4H), 6.44 (d, J=8 Hz, 1H), 4.62 (s, 2H), 4.62-4.53 (br, 2H), 3.81-3.79 (m, 4H), 3.01-2.98 (m, 4H).

Sources & evidence

ORD record
ord-31d03f9a40ae4b4692cd0a36179d1f2d
Source dataset
uspto-grants-2008_10
Patent number
US07432288B2

Reaction notes

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