Piperonylamine → 8-methyl-5-(2-(6-(trifluoromethyl)pyridin-3-yl)ethyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

HRID 1773250노트

반응식

HRID 1773250 반응식
[C:1]1([CH3:21])[CH:6]=[CH:5][C:4]([N:7]([CH2:9][CH2:10][C:11]2[CH:12]=[CH:13][C:14]([C:17]([F:20])([F:19])[F:18])=[N:15][CH:16]=2)N)=[CH:3][CH:2]=1.Cl.O.[NH:24]1[CH2:29][CH2:28][C:27](=O)[CH2:26][CH2:25]1>O1CCOCC1.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>[CH3:21][C:1]1[CH:6]=[CH:5][C:4]2[N:7]([CH2:9][CH2:10][C:11]3[CH:16]=[N:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=3)[C:27]3[CH2:28][CH2:29][NH:24][CH2:25][C:26]=3[C:3]=2[CH:2]=1

참가 물질

6

반응물 2

HCID 2723901PiperonylamineHCID 666017985-(2-(1-p-Tolylhydrazinyl)ethyl)-2-(trifluoromethyl)pyridine

생성물 1

HCID 497799108-methyl-5-(2-(6-(trifluoromethyl)pyridin-3-yl)ethyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

시약·촉매·용매 3

HCID 6422Trifluoroacetic acid촉매HCID 312751,4-Dioxane용매HCID 516892Sodium Bicarbonate용매

반응 조건

온도
100 °C

실험 절차

5-(2-(1-p-Tolylhydrazinyl)ethyl)-2-(trifluoromethyl)pyridine (88 mg, 0.29 mmol) was dissolved in 1,4-dioxane (2 mL) and 4-piperidone hydrate hydrochloride was added with one drop of TFA. The reaction mixture became acidic. The mixture was heated at 100° C. for 2 h. The reaction was monitored by TLC and LCMS. After completion of reaction, the mixture was diluted with sat. NaHCO3 solution and extracted with EtOAc. The organic extracts were dried over anhydrous sodium sulfate and concentrated. The compound was purified by reverse phase chromatography. 1HNMR (CD3OD, TFA salt) d (ppm): 8.20 (s, 1H), 7.60 (m, 2H), 7.25 (d, 1H), 7.18 (d, 1H), 6.98 (d, 1H), 4.40 (m, 4H), 3.50 (t, 2H), 3.20 (m, 2H), 2.82 (t, 2H), 2.40 (s, 3H).

후처리

  1. customAfter completion of reaction
  2. extractionextracted with EtOAc
  3. dry with materialThe organic extracts were dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe compound was purified by reverse phase chromatography

출처 및 근거

ORD 기록
ord-7b2280d4ac3642bb92b9cec848984728
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09255094B2

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