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Lawesson's reagent → 4-thioxo-1-(4-{(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}butyl)-3,4-dihydro-2(1H)-pyrimidinone hydrochloride

HRID 12782
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인쇄 미리보기

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HRID 12782 반응식
[ClH:1].[F:2][C:3]([F:29])([F:28])[C:4]1[CH:9]=[CH:8][C:7]([C@:10]23[CH2:15][C@H:14]2[CH2:13][N:12]([CH2:16][CH2:17][CH2:18][CH2:19][N:20]2[CH:25]=[CH:24][C:23](=O)[NH:22][C:21]2=[O:27])[CH2:11]3)=[CH:6][CH:5]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:39])=CC=1>COCCOC>[ClH:1].[S:39]=[C:23]1[CH:24]=[CH:25][N:20]([CH2:19][CH2:18][CH2:17][CH2:16][N:12]2[CH2:13][C@H:14]3[C@:10]([C:7]4[CH:8]=[CH:9][C:4]([C:3]([F:29])([F:28])[F:2])=[CH:5][CH:6]=4)([CH2:15]3)[CH2:11]2)[C:21](=[O:27])[NH:22]1
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참가 물질

4

반응물 2

HCID 87949Lawesson's reagentHCID 686914601-(4-{(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}butyl)-2,4(1H,3H)-pyrimidinedione hydrochloride

생성물 1

HCID 866159544-thioxo-1-(4-{(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}butyl)-3,4-dihydro-2(1H)-pyrimidinone hydrochloride수율 63%

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

실험 절차

A solution of 1-(4-{(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}butyl)-2,4(1H,3H)-pyrimidinedione (E5, 110 mg, 0.3 mmol) and Lawesson's reagent (184 mg, 0.5 mmol) in DME (2 mL) was stirred at reflux for 2 hours. The solvent was evaporated under vacuum. The crude was re-dissolved in ethyl acetate and washed with water. The organic phase was dried (Na2SO4) filtered and evaporated; the crude was purified by flash chromatography with DCM-MeOH—NH4OH (98-2-0.2) to give the title compound as a yellow oil (80 mg, 63% yield).

후처리

  1. temperatureat reflux for 2 hours
  2. customThe solvent was evaporated under vacuum
  3. dissolutionThe crude was re-dissolved in ethyl acetate
  4. washwashed with water
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customthe crude was purified by flash chromatography with DCM-MeOH—NH4OH (98-2-0.2)

출처 및 근거

ORD 기록
ord-fb66b91e750f4f81a06e92bdd42c658d
출처 데이터셋
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07727988B2

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