Dimethylformamide → Cyclohexanecarboxamide

HRID 410549

Reaktionsgleichung

Reaktionsgleichung von HRID 410549
[Cl-].[NH4+].CN(C(ON1N=N[C:13]2[CH:14]=[CH:15][CH:16]=[N:17][C:12]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N([CH:33]([CH3:35])C)CC)(C)C.CN(C)C=[O:39]>O>[CH:13]1([C:12]([NH2:17])=[O:39])[CH2:14][CH2:15][CH2:16][CH2:35][CH2:33]1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Produkt 1

HCID 14283CyclohexanecarboxamideAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

cis-4-Hydroxy-4-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]cyclohexanecarboxylic acid (500 mg, 1.05 mmol), ammonium chloride (112 mg, 2.09 mmol), 0-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (795 mg, 2.09 mmol), and diisopropylethylamine (730 μl, 4.18 mmol) were taken-up in dimethylformamide (4.2 mL) under argon. The vessel was sealed and stirred at 65° C. for 4 hours. Upon cooling, the reaction mixture was diluted with water, and the resulting precipitate was collected via filtration. The solids were washed with water and diethyl ether and dried in vacuo overnight to afford cis-4-hydroxy-4-[5-(3-methyl-5-{[4-Orifluoromethyl)pyrimidin-2-yl]amino}-phenyl)-1,3-thiazol-2-yl]cyclohexanecarboxamide (437.6 mg, 0.916 mmol, 88% yield) as a white solid. MS ESI: [M+H]+ m/z 478.1.

Aufarbeitung

  1. customThe vessel was sealed
  2. temperatureUpon cooling
  3. filtrationthe resulting precipitate was collected via filtration
  4. washThe solids were washed with water and diethyl ether
  5. customdried in vacuo overnight

Quellen und Nachweise

ORD-Eintrag
ord-55a704798d9848d4a5415133f0b7ea22
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08759366B2

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