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

HRID 1873841

Reaktionsgleichung

Reaktionsgleichung von HRID 1873841
[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

Komponenten

7

Edukt 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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 25517Ammonium ChlorideLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-f51855d3f41243778c9704316ca560cd
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08304434B2

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