Methanol → HCID 10150756, compound

HRID 1582154Notes

Reaction equation

[CH3:1][OH:2].[H-].[Na+].Br[C:6]1[CH:7]=[C:8]([CH:29]=[CH:30][N:31]=1)[C:9]([NH:11][C:12]1[S:13][C:14]2[C:20]([CH:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)=[CH:19][CH:18]=[C:17]([O:27][CH3:28])[C:15]=2[N:16]=1)=[O:10]>O1CCOCC1>[CH3:1][O:2][C:6]1[CH:7]=[C:8]([CH:29]=[CH:30][N:31]=1)[C:9]([NH:11][C:12]1[S:13][C:14]2[C:20]([CH:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)=[CH:19][CH:18]=[C:17]([O:27][CH3:28])[C:15]=2[N:16]=1)=[O:10]

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred solution of 0.09 ml (2.23 mmol) methanol in 5 ml dioxane at room temperature was added 49 mg (1.12 mmol) sodium hydride (55% dispersion in mineral oil) and the mixture heated at 50° C. for 1 hour. 100 mg (0.22 mmol) 2-bromo-N-[4-methoxy-7-(tetrahydro-pyran-4-yl)-benzothiazol-2-yl]-isonicotinamide was then added and the mixture heated at 50° 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 (ethyl acetate) followed by trituration in ether and hexane afforded 60 mg (67%) 2-methoxy-N-[4-methoxy-7-(tetrahydro-pyran-4-yl)-benzothiazol-2-yl]-isonicotinamide as a white crystalline solid. ES-MS m/e (%): 398 ([M−H]−, 100).

Workup

temperaturethe mixture heated at 50° 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-083b3c01815f44398ebac0ce2761d069
Source dataset: uspto-grants-2004_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06734179B2

Reaction notes

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