Morpholine → HCID 10238546, compound

HRID 51848Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][N:27]=1)[C:5]([NH:7][C:8]1[S:9][C:10]2[C:16]([N:17]([CH2:19][CH2:20][O:21][CH3:22])[CH3:18])=[CH:15][CH:14]=[C:13]([O:23][CH3:24])[C:11]=2[N:12]=1)=[O:6].[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN1CCCC1=O>[CH3:24][O:23][C:13]1[C:11]2[N:12]=[C:8]([NH:7][C:5](=[O:6])[C:4]3[CH:25]=[CH:26][N:27]=[C:2]([N:28]4[CH2:33][CH2:32][O:31][CH2:30][CH2:29]4)[CH:3]=3)[S:9][C:10]=2[C:16]([N:17]([CH2:19][CH2:20][O:21][CH3:22])[CH3:18])=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 140 °C

Procedure

A stirred suspension of 200 mg (0.44 mmol) 2-bromo-N-{4-methoxy-7-[(2-methoxy-ethyl)-methyl-amino]-benzothiazol-2-yl}-isonicotinamide, 0.38 ml (4.43 mmol) morpholine and 289 mg (0.89 mmol) cesium carbonate in 5 ml N-methylpyrrolidone in a thick-walled glass pressure tube fitted with a teflon cap was heated at 140° C. for 24 h. The reaction mixture was then cooled to room temperature and poured onto water. The mixture was extracted three times with ethyl acetate, and the combined organic phases were dried over sodium sulfate and concentrated in vacuo. Flash chromatography (ethyl acetate) followed by trituration in ether afforded 100 mg (49%) N-{4-methoxy-7-[(2-methoxy-ethyl)-methyl-amino]-benzothiazol-2-yl}-2-morpholin-4-yl-isonicotinamide as a light yellow crystalline solid. ES-MS m/e (%): 458 (M+H+, 100).

Workup

customcap
temperatureThe reaction mixture was then cooled to room temperature
additionpoured onto water
extractionThe mixture was extracted three times with ethyl acetate
dry with materialthe combined organic phases were dried over sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-1886fefd940748f1b347be279076bea3
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06713499B2

Reaction notes

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