Dimethylformamide → Cyclohexanecarboxamide

HRID 410549

Reaction equation

HRID 410549 reaction equation
[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

Participants

6

Reactant 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)

Product 1

HCID 14283CyclohexanecarboxamideYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-55a704798d9848d4a5415133f0b7ea22
Source dataset
uspto-grants-2014_06
Patent number
US08759366B2

Linked notes

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