Morpholine → HCID 10238546, 화합물

HRID 51848노트

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HRID 51848 반응식
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

참가 물질

5

반응물 3

HCID 8083MorpholineHCID 10796Cesium carbonateHCID 227369762-Bromo-N-{4-methoxy-7-[(2-methoxy-ethyl)-methyl-amino]-benzothiazol-2-yl}-isonicotinamide

생성물 1

HCID 10238546HCID 10238546, 화합물수율 49.7%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

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온도
140 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-1886fefd940748f1b347be279076bea3
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06713499B2

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