Ethanol → HCID 22993419, compound

HRID 1167764Notes

Reaction equation

[CH2:1]([OH:3])[CH3:2].[H-].[Na+].Cl[C:7]1[CH:32]=[CH:31][C:10]([C:11]([NH:13][C:14]2[S:15][C:16]3[C:22]([N:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)=[CH:21][CH:20]=[C:19]([O:29][CH3:30])[C:17]=3[N:18]=2)=[O:12])=[CH:9][N:8]=1>O1CCOCC1>[CH2:1]([O:3][C:7]1[CH:32]=[CH:31][C:10]([C:11]([NH:13][C:14]2[S:15][C:16]3[C:22]([N:23]4[CH2:24][CH2:25][O:26][CH2:27][CH2:28]4)=[CH:21][CH:20]=[C:19]([O:29][CH3:30])[C:17]=3[N:18]=2)=[O:12])=[CH:9][N:8]=1)[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred solution of 0.24 ml (4.94 mmol) ethanol in 5 ml dioxane at room temperature was added 270 mg (6.18 mmol) sodium hydride (55% dispersion in mineral oil) and the mixture heated at 50° C. for 30 min. 500 mg (1.23 mmol) 6-chloro-N-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-nicotinamide was then added and the mixture heated at 80° C. for 16 h. The reaction mixture was then cooled to room temperature and poured onto water. The mixture was extracted three times with dichloromethane, and the combined organic phases were dried over sodium sulfate and concentrated in vacuo. Flash chromatography (1/99 methanol/dichloromethane) followed by trituration in ether afforded 270 mg (53%) 6-ethoxy-N-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-nicotinamide as a white crystalline solid. ES-MS m/e (%): 437 (M+Na+, 26), 415 (M+H+, 100).

Workup

temperaturethe mixture heated at 80° C. for 16 h
temperatureThe reaction mixture was then cooled to room temperature
additionpoured onto water
extractionThe mixture was extracted three times with dichloromethane
dry with materialthe combined organic phases were dried over sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-3f5bd2821b024d40b58c6b484fdf8b56
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06620811B2

Reaction notes

Loading…