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N-methyl-2-pyrrolidone → 2-(1,1-Dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-6-methyl-N-(2-methylprop-2-en-1-yl)quinolin-4-amine

HRID 540229
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HRID 540229 반응식
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9](OC(F)(F)F)[CH:10]=2)[N:5]=[C:4]([N:17]2[CH2:23][C:22]3[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=3[S:20](=[O:29])(=[O:28])[CH2:19][CH2:18]2)[CH:3]=1.[CH3:30][C:31](=[CH2:34])[CH2:32][NH2:33].[CH3:35]N1CCCC1=O>O>[O:28]=[S:20]1(=[O:29])[C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[CH2:23][N:17]([C:4]2[CH:3]=[C:2]([NH:33][CH2:32][C:31]([CH3:30])=[CH2:34])[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([CH3:35])[CH:10]=3)[N:5]=2)[CH2:18][CH2:19]1
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참가 물질

5

반응물 3

HCID 13387N-methyl-2-pyrrolidoneHCID 761412-MethylallylamineHCID 712545694-(4-Chloro-6-(trifluoromethoxy)quinolin-2-yl)-2,3,4,5-tetrahydro-1,4-benzothiazepine 1,1-dioxide

생성물 1

HCID 866914132-(1,1-Dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-6-methyl-N-(2-methylprop-2-en-1-yl)quinolin-4-amine

시약·촉매·용매 1

HCID 962Water용매

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온도
160 °C

실험 절차

A solution of 4-(4-chloro-6-methylquinolin-2-yl)-2,3,4,5-tetrahydro-1,4-benzothiazepine 1,1-dioxide (372.0 mg, 1.0 mmol, prepared in analogy to 4-(4-chloro-6-(trifluoromethoxy)quinolin-2-yl)-2,3,4,5-tetrahydro-1,4-benzothiazepine 1,1-dioxide in Example 17-1) and 2-methylprop-2-en-1-amine (213.0 mg, 3.0 mmol) in 1-methyl-2-pyrrolidinone (1.0 mL) was heated with stirring at 160° C. for 36 hours. The reaction mixture was cooled to room temperature, diluted with water (10 mL) and extracted with ethyl acetate (100 mL). The organic layer was washed with brine (50 mL×2), dried over anhydrous sodium sulfate and then concentrated in vacuo to afford 407.0 mg of the product as a light yellow solid. MS obsd. (ESI+) [(M+H)+] 408.

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate (100 mL)
  3. washThe organic layer was washed with brine (50 mL×2)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-2f5d260dc502405c9f7a7cb7335b2994
출처 데이터셋
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08871756B2

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