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Potassium Carbonate → 2-[3,5-Bis(trifluoromethyl)phenyl]-N-[6-(1,1-dioxidohexahydro-5H-isothiazolo[2,3-a]pyrazin-5-yl)-4-(2-methylphenyl)-3-pyridinyl]-N,2-dimethylpropanamide

HRID 2245462
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HRID 2245462 반응식
[F:1][C:2]([F:35])([F:34])[C:3]1[CH:4]=[C:5]([C:13]([CH3:33])([CH3:32])[C:14]([N:16]([C:18]2[CH:19]=[N:20][C:21](Cl)=[CH:22][C:23]=2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH3:30])[CH3:17])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[S:36]1(=[O:46])(=[O:45])[N:40]2[CH2:41][CH2:42][NH:43][CH2:44][CH:39]2[CH2:38][CH2:37]1.C(=O)([O-])[O-].[K+].[K+].[NH4+].[Cl-]>CS(C)=O>[F:1][C:2]([F:35])([F:34])[C:3]1[CH:4]=[C:5]([C:13]([CH3:33])([CH3:32])[C:14]([N:16]([C:18]2[CH:19]=[N:20][C:21]([N:43]3[CH2:42][CH2:41][N:40]4[S:36](=[O:46])(=[O:45])[CH2:37][CH2:38][CH:39]4[CH2:44]3)=[CH:22][C:23]=2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH3:30])[CH3:17])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1
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참가 물질

6

반응물 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 102295322-(3,5-bis(trifluoromethyl)phenyl)-N-(6-chloro-4-(o-tolyl)pyridin-3-yl)-N,2-dimethylpropanamideHCID 59215775Hexahydro-2H-isothiazolo[2,3-a]pyrazine 1,1-dioxide

생성물 1

HCID 160636472-[3,5-Bis(trifluoromethyl)phenyl]-N-[6-(1,1-dioxidohexahydro-5H-isothiazolo[2,3-a]pyrazin-5-yl)-4-(2-methylphenyl)-3-pyridinyl]-N,2-dimethylpropanamide
수율 75.9%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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온도
180 °C

실험 절차

The title compound was prepared starting from 100 mg (0.161 mmoles) of 2-[3,5-bis(trifluoromethyl)phenyl]-N-[6-chloro-4-(2-methylphenyl)-3-pyridinyl]-N,2-dimethylpropanamide (WO 2005/002577), 85 mg (0.483 mmol) of hexahydro-2H -isothiazolo[2,3-a ] pyrazine 1,1-dioxide (D10), 44.5 mg (0.322 mmol) of potassium carbonate; the reagents were dissolved in 0.8 ml of DMSO . The reaction mixture was heated at 180° C. for 36-48 hrs and then added to a saturated NH4Cl solution and back extracted with DCM; the crude material was purified on SPE cartridge (Silica) eluting with a gradient from cyclohexane/ethyl acetate 9:1, to cyclohexane/ethyl acetate 1:1 and affording 80 mg of the title compound as pale yellow solid.

후처리

  1. customThe title compound was prepared
  2. extractionback extracted with DCM
  3. customthe crude material was purified on SPE cartridge (Silica)
  4. washeluting with a gradient from cyclohexane/ethyl acetate 9:1, to cyclohexane/ethyl acetate 1:1

출처 및 근거

ORD 기록
ord-5b239a58ea914319b9a980c4efa015d3
출처 데이터셋
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07683056B2

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