Diisopropylethylamine → 2-(Cyclopropylsulfonyl)-3-{[4-(1-methyl-1-{[3-(trifluoromethyl)phenyl]sulfonyl}ethyl)piperidin-1-yl]carbonyl}-6-(trifluoromethyl)pyridine

HRID 1873841노트

반응식

HRID 1873841 반응식
[CH3:1][C:2]([CH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)([S:4]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=1)(=[O:6])=[O:5])[CH3:3].[CH:23]1([S:26]([C:29]2[N:37]=[C:36]([C:38]([F:41])([F:40])[F:39])[CH:35]=[CH:34][C:30]=2[C:31](O)=[O:32])(=[O:28])=[O:27])[CH2:25][CH2:24]1.CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>[NH4+].[Cl-].CN(C)C=O>[CH:23]1([S:26]([C:29]2[C:30]([C:31]([N:20]3[CH2:21][CH2:22][CH:17]([C:2]([CH3:1])([S:4]([C:7]4[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:14])([F:16])[F:15])[CH:8]=4)(=[O:5])=[O:6])[CH3:3])[CH2:18][CH2:19]3)=[O:32])=[CH:34][CH:35]=[C:36]([C:38]([F:41])([F:40])[F:39])[N:37]=2)(=[O:27])=[O:28])[CH2:25][CH2:24]1

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 594474094-(1-Methyl-1-{[3-(trifluoromethyl)phenyl]sulfonyl}ethyl)piperidineHCID 684877982-(Cyclopropylsulfonyl)-6-(trifluoromethyl)nicotinic acid

생성물 1

HCID 252557852-(Cyclopropylsulfonyl)-3-{[4-(1-methyl-1-{[3-(trifluoromethyl)phenyl]sulfonyl}ethyl)piperidin-1-yl]carbonyl}-6-(trifluoromethyl)pyridine

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 25517Ammonium Chloride용매

실험 절차

To a 50 ml round bottom flask was added 4-(1-methyl-1-{[3-(trifluoromethyl)phenyl]sulfonyl}ethyl)piperidine (1.64 g, 4.88 mmol), 2-(cyclopropylsulfonyl)-6-(trifluoromethyl)nicotinic acid (1.2 g, 4.06 mmol), Bop reagent (2.16 g, 4.88 mmol), diisopropylethyl amine (1.42 ml, 8.13 mmol) and 10 ml dimethylformamide. The resulting solution was stirred at room temperature 10 minutes. It was diluted with 60 ml NH4Cl solution and extracted with 60 ml ethyl acetate. The organics were dried over sodium sulfate, filtered and concentrated. The sesidue was purified on silica gel column eluted with 2:1 ethyl acetate/hexane. The desired fraction was collected and concentrated. The residue was further purified on prep-TLC to give title compound as a white solid.

후처리

  1. extractionextracted with 60 ml ethyl acetate
  2. dry with materialThe organics were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe sesidue was purified on silica gel column
  6. washeluted with 2:1 ethyl acetate/hexane
  7. customThe desired fraction was collected
  8. concentrationconcentrated
  9. customThe residue was further purified on prep-TLC

출처 및 근거

ORD 기록
ord-f51855d3f41243778c9704316ca560cd
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08304434B2

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