Water → HCID 22636132, compound

HRID 502051Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8](Cl)=[O:9])=[CH:4][CH:3]=1.[NH2:11][C:12]1[CH:13]=[C:14]([CH:31]=[CH:32][C:33]=1[Cl:34])[C:15]([NH:17][C:18]1[CH:23]=[C:22]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[CH:21]=[C:20]([F:30])[CH:19]=1)=[O:16].N1C=CC=CC=1.O>C(OCC)C>[Cl:34][C:33]1[CH:32]=[CH:31][C:14]([C:15]([NH:17][C:18]2[CH:23]=[C:22]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)[CH:21]=[C:20]([F:30])[CH:19]=2)=[O:16])=[CH:13][C:12]=1[NH:11][C:8]([C:5]1[CH:6]=[N:7][C:2]([Cl:1])=[CH:3][CH:4]=1)=[O:9]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 6-chloropyrid-3-ylcarbonyl chloride (1.96 g), 3-amino-4-chloro-N-(3-fluoro-5-morpholinophenyl)benzamide (3 g) and pyridine (20 ml) was stirred and heated to 100° C. for 4 hours. The mixture was cooled to ambient temperature. Water and diethyl ether were added. The resultant precipitate was washed with a saturated aqueous sodium bicarbonate solution and with methanol. There was thus obtained the title compound (3.8 g); NMR Spectrum: (DMSOd6) 3.1 (t, 4H), 3.75 (t, 4H), 6.52 (d, 1H), 7.1 (s, 1H), 7.2 (d, 1H), 7.6-7.7 (m, 2H), 7.7-7.8 (m, 1H), 8.2 (d, 1H), 8.35-8.4 (m, 1H), 8.97 (d, 1H), 10.2-10. 32 (br S, 1H); Mass Spectrum: M+H+ 489.

Workup

temperatureThe mixture was cooled to ambient temperature
washThe resultant precipitate was washed with a saturated aqueous sodium bicarbonate solution and with methanol

Sources & evidence

ORD record: ord-f0b269803c654711b684f597319a9d37
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07772432B2

Reaction notes

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