2-Methoxyethanol → HCID 10216884, compound

HRID 1167733Notes

Reaction equation

[CH3:1][O:2][CH2:3][CH2:4][OH:5].[H-].[Na+].Cl[C:9]1[CH:10]=[C:11]([CH:32]=[CH:33][N:34]=1)[C:12]([NH:14][C:15]1[S:16][C:17]2[C:23]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)=[CH:22][CH:21]=[C:20]([O:30][CH3:31])[C:18]=2[N:19]=1)=[O:13]>O1CCOCC1.C(OCC)(=O)C>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:9]1[CH:10]=[C:11]([CH:32]=[CH:33][N:34]=1)[C:12]([NH:14][C:15]1[S:16][C:17]2[C:23]([N:24]3[CH2:25][CH2:26][O:27][CH2:28][CH2:29]3)=[CH:22][CH:21]=[C:20]([O:30][CH3:31])[C:18]=2[N:19]=1)=[O:13]

Participants

Conditions

Temperature: 115 °C

Procedure

To a stirred solution of 0.058 ml (0.74 mmol) 2-methoxyethanol in 2 ml dioxane at room temperature was added 49 mg (1.24 mmol) sodium hydride (60% dispersion in mineral oil) and stirring continued for 10 minutes. 200 mg (0.49 mmol) 2-chloro-N-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-isonicotinamide was then added and the mixture heated at 115° C. for 16 h. The reaction mixture was then cooled to room temperature, diluted with ethyl acetate, and washed sequentially with 1 M hydrochloric acid and saturated brine. The organic phase was then dried over sodium sulfate and concentrated in vacuo. Flash chromatography (2/1 ethyl acetate/toluene) afforded 109 mg (50%) 2-(2-methoxy-ethoxy)-N-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-isonicotinamide as a yellow crystalline solid. ES-MS m/e (%): 467 (M+Na+, 16), 445 (M+H+, 100).

Workup

temperatureThe reaction mixture was then cooled to room temperature
washwashed sequentially with 1 M hydrochloric acid and saturated brine
dry with materialThe organic phase was then dried over sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-06ced4a6bff54ea0bf36a4e8b0e072ed
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06620811B2

Reaction notes

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