Diisopropylethylamine → 1-[2-(Methylsulfonyl)-4-(trifluoromethoxy)benzoyl]-4-(1-methyl-1-{[3-(trifluoromethyl)phenyl]sulfonyl}ethyl)piperidine

HRID 1873839Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1873839
[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].[CH3:23][S:24]([C:27]1[CH:35]=[C:34]([O:36][C:37]([F:40])([F:39])[F:38])[CH:33]=[CH:32][C:28]=1[C:29](O)=[O:30])(=[O:26])=[O:25].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>CS(C)=O.O.FC(F)(F)C(O)=O.CN(C)C=O>[CH3:23][S:24]([C:27]1[CH:35]=[C:34]([O:36][C:37]([F:38])([F:39])[F:40])[CH:33]=[CH:32][C:28]=1[C:29]([N:20]1[CH2:21][CH2:22][CH:17]([C:2]([CH3:1])([S:4]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:14])([F:16])[F:15])[CH:8]=2)(=[O:5])=[O:6])[CH3:3])[CH2:18][CH2:19]1)=[O:30])(=[O:26])=[O:25]

Komponenten

9

Edukt 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 59447309HCID 59447309, VerbindungHCID 594474094-(1-Methyl-1-{[3-(trifluoromethyl)phenyl]sulfonyl}ethyl)piperidine

Produkt 1

HCID 252557841-[2-(Methylsulfonyl)-4-(trifluoromethoxy)benzoyl]-4-(1-methyl-1-{[3-(trifluoromethyl)phenyl]sulfonyl}ethyl)piperidine

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

To a 10 ml vial was added 4-(1-methyl-1-{[3-(trifluoromethyl)phenyl]sulfonyl}ethyl)piperidine (70.8 mg, 0.211 mmol), 2-(methylsulfonyl)-4-(trifluoromethoxy)benzoic acid (50 mg, 0.176 mmol), Bop reagent (93 mg, 0.211 mmol), diisopropylethyl amine (0.062 ml, 0.352 mmol) and 2 ml dimethylformamide. The resulting solution was stirred at room temperature for 10 minutes. The reaction mixture was diluted with 1 ml dimethyl sulfoxide, 1 ml water and 0.03 ml of trifluoroacetic acid. This mixture was loaded on a reverse phase column and purified with HPLC eluted with water/acetonitrile gradient solvent. Desired fraction was collected and lyophilized to give to give title compound as fluffy white solid.

Aufarbeitung

  1. custompurified with HPLC
  2. washeluted with water/acetonitrile gradient solvent
  3. customDesired fraction was collected
  4. customto give

Quellen und Nachweise

ORD-Eintrag
ord-66f474659cc04294a5f14145823fbc0c
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08304434B2

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