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

HRID 1773250ノート

反応式

HRID 1773250 の反応式
[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

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 6422Trifluoroacetic acid触媒HCID 312751,4-Dioxane溶媒HCID 516892Sodium Bicarbonate溶媒

反応条件

温度
100 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-7b2280d4ac3642bb92b9cec848984728
出典データセット
uspto-grants-2016_02
特許番号
US09255094B2

反応ノート

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