Acetonitrile → 2-(1-(Methylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl)-5-((1-((1-(trifluoromethyl)cyclopropyl)methyl)piperidin-4-yl)methoxy)pyridine

HRID 222597노트

반응식

HRID 222597 반응식
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH2:23][CH2:24][N:25]([S:28]([CH3:31])(=[O:30])=[O:29])[CH2:26][CH:27]=3)=C[C:17]=2F)[CH2:10][CH2:9]1)=O)(C)(C)C.C(=O)([O-])[O-].[K+].[K+].C(#[N:41])C.CS(O[CH2:47][C:48]1([C:51]([F:54])([F:53])[F:52])[CH2:50][CH2:49]1)(=O)=O>ClCCl.O>[CH3:31][S:28]([N:25]1[CH2:26][CH:27]=[C:22]([C:19]2[CH:20]=[CH:21][C:16]([O:15][CH2:14][CH:11]3[CH2:12][CH2:13][N:8]([CH2:47][C:48]4([C:51]([F:52])([F:53])[F:54])[CH2:49][CH2:50]4)[CH2:9][CH2:10]3)=[CH:17][N:41]=2)[CH2:23][CH2:24]1)(=[O:30])=[O:29]

참가 물질

7

반응물 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 668644984-[2-Fluoro-4-(1-methanesulfonyl-1,2,3,6-tetrahydro-pyridin-4-yl)-phenoxymethyl]-piperidine-1-carboxylic acid tert-butyl esterHCID 86649942(1-(Trifluoromethyl)cyclopropyl)methyl methanesulfonate

생성물 1

HCID 581111522-(1-(Methylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl)-5-((1-((1-(trifluoromethyl)cyclopropyl)methyl)piperidin-4-yl)methoxy)pyridine수율 65.2%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

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온도
140 °C

실험 절차

To Preparation 6 (206 mg, 0.586 mmol), potassium carbonate (243 mg, 1.76 mmol) and acetonitrile (2.93 mL, 56 mmol) in a microwave vial is added (1-(trifluoromethyl)cyclopropyl)methyl methanesulfonate (256 mg, 1.17 mmol). The microwave vial is sealed and heated at 140° C. for 2 h then 150° C. for 30 min in the Biotage microwave. The reaction is diluted with dichloromethane and water. The organic layer is separated and washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue is triturated with diethylether and the title product is collected via vacuum filtration to obtain 0.181 g of the title compound. MS (m/z) 474 (M+1).

후처리

  1. customThe microwave vial is sealed
  2. customThe organic layer is separated
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is triturated with diethylether
  8. filtrationthe title product is collected via vacuum filtration

출처 및 근거

ORD 기록
ord-e3b419b5ca9c479392ca8f560c5c9e17
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207344B2

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