Trifluoroacetic acid → HCID 86633884, compound

HRID 1687147Notes

Reaction equation

HRID 1687147 reaction equation
C(O[C:6](=O)[NH:7][C@@H:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]1[C:14](=[O:16])[NH2:15])(C)(C)C.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+].[Cl:30][C:31]1[N:36]=C(Cl)[C:34]([Cl:38])=[CH:33][N:32]=1>C(Cl)Cl.O.CO>[Cl:30][C:31]1[N:36]=[C:6]([NH:7][C@@H:8]2[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]2[C:14]([NH2:15])=[O:16])[C:34]([Cl:38])=[CH:33][N:32]=1

Participants

8

Reactant 4

HCID 6422Trifluoroacetic acidHCID 2372592,4,5-TrichloropyrimidineHCID 516892Sodium BicarbonateHCID 67263918HCID 67263918, compound

Product 1

HCID 86633884HCID 86633884, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

trans-(2-Carbamoyl-cyclohexyl)-carbamic acid tert-butyl ester (246.5 mg, 1.02 mmol, J. Molec. Cat. B: Enzymatic, 2004, 29, 115-121) was dissolved in DCM and treated with TFA (5 mL). After 2 h, solvent was removed by rotary evaporation and the residue was repeated evaporated from CHCl3 to remove any trace of TFA. To this residue was sequentially added MeOH (3 mL), water (1.5 mL), NaHCO3 (171.2 mg, 2.04 mmol) and 2,4,5-trichloropyrimidine (224 mg, 1.22 mmol). After stirring for 40 h, addition of water (3 mL) gave a precipitate that was removed by filtration and washed with water (5×2 mL) and ether (2×2 mL) to afford 2-(2,5-dichloro-pyrimidin-4-ylamino)-trans-cyclohexanecarboxylic acid amide as a white solid that was used without further purification in the subsequent step.

Workup

  1. customsolvent was removed by rotary evaporation
  2. customthe residue was repeated evaporated from CHCl3
  3. customto remove any trace of TFA
  4. customgave a precipitate that
  5. customwas removed by filtration
  6. washwashed with water (5×2 mL) and ether (2×2 mL)

Sources & evidence

ORD record
ord-4e1decb023ff4c79b0859fdec25d72bf
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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