Benzenamine, 4-(4-morpholinyl)- → HCID 11407140, compound

HRID 2113755Notes

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.[O:19]1[CH2:24][CH2:23][N:22]([C:25]2[CH:31]=[CH:30][C:28]([NH2:29])=[CH:27][CH:26]=2)[CH2:21][CH2:20]1>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:28]2[CH:27]=[CH:26][C:25]([N:22]3[CH2:23][CH2:24][O:19][CH2:20][CH2:21]3)=[CH:31][CH:30]=2)[C:3]1=[O:18]

Participants

Conditions

Temperature: 130 °C

Procedure

3-Chloro-1-(2-methoxyethyl)-4-phenyl-1H-pyrrole-2,5-dione (0.26 mmol, 70 mg) and 4-morpholinoaniline (0.53 mmol, 94 mg) was dissolved in dry CH3CN (2 mL) and the reaction mixture was subjected to microwave heating single node 130° C. for 10 min and purified on SiO2 (EtOAc:heptane, 1:1) to give 96 mg (89%) of the title compound. 1H NMR (400 MHz, CD3CN) δ 7.73 (bs, 1H), 7.17-7.04 (m, 3H), 6.98-6.93 (m, 2H), 6.70-6.64 (m, 2H), 6.59-6.54 (m, 2H), 3.75-3.70 (m, 6H), 3.58 (t, J=5.6 Hz, 2H), 3.33 (s, 3H), 2.98-2.95 (m, 4H).

Workup

custompurified on SiO2 (EtOAc:heptane, 1:1)

Sources & evidence

ORD record: ord-f0bf7873eda9484085f9dbc1b43a0d9e
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07432288B2

Reaction notes

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