Cyclohexylamine → 2-methyl-1-[(S)-1-(tetrahydro-furan-2-yl)methyl]-5-(2-trifluoromethoxy-phenyl)-1H-pyrrole-3-carboxylic acid cyclohexylamide

HRID 229862

Reaktionsgleichung

Reaktionsgleichung von HRID 229862
[CH3:1][C:2]1[N:3]([CH2:21][C@@H:22]2[CH2:26][CH2:25][CH2:24][O:23]2)[C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][C:17]([F:20])([F:19])[F:18])=[CH:5][C:6]=1[C:7](O)=[O:8].CN(C(O[N:35]1N=N[C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][C:36]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)C(C)C)(C)C.C1(N)CCCCC1>CN(C)C=O>[CH:36]1([NH:35][C:7]([C:6]2[CH:5]=[C:4]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[O:16][C:17]([F:18])([F:19])[F:20])[N:3]([CH2:21][C@@H:22]3[CH2:26][CH2:25][CH2:24][O:23]3)[C:2]=2[CH3:1])=[O:8])[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1

Komponenten

6

Edukt 4

HCID 7965CyclohexylamineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 690199812-methyl-1-[(S)-1-(tetrahydro-furan-2-yl)methyl]-5-(2-trifluoromethoxy-phenyl)-1H-pyrrole-3-carboxylic acid

Produkt 1

HCID 116193132-methyl-1-[(S)-1-(tetrahydro-furan-2-yl)methyl]-5-(2-trifluoromethoxy-phenyl)-1H-pyrrole-3-carboxylic acid cyclohexylamideAusbeute 74,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 77 mg of 2-methyl-1-[(S)-1-(tetrahydro-furan-2-yl)methyl]-5-(2-trifluoromethoxy-phenyl)-1H-pyrrole-3-carboxylic acid in 3 ml of dimethylformamide were added 74 mg of TBTU, 179 μl of N,N-diisopropylethylamine and 26 μl of cyclohexylamine and the reaction mixture was stirred at ambient temperature for 18 hours. After such time the reaction mixture was then concentrated in vacuo and purified by column chromatography (SiO2, heptane/ethyl acetate) to give 70 mg of the title compound as a colorless solid, MS (ISP) 451.5 (M+H)+.

Aufarbeitung

  1. concentrationAfter such time the reaction mixture was then concentrated in vacuo
  2. custompurified by column chromatography (SiO2, heptane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-98c6549fcfc146cfbf597b08fa7994f7
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07563910B2

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