Hydrochloric Acid → HCID 9913704, compound

HRID 379404Notes

Reaction equation

HRID 379404 reaction equation
C([NH:8][C:9]1[N:14]=[CH:13][C:12]([N:15]([CH3:35])[C:16](=[O:34])[C:17]([C:20]2[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[C:22]([C:30]([F:33])([F:32])[F:31])[CH:21]=2)([CH3:19])[CH3:18])=[C:11]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=2[CH3:42])[CH:10]=1)C1C=CC=CC=1.Cl>C(O)C.CO.[Pd]>[NH2:8][C:9]1[N:14]=[CH:13][C:12]([N:15]([CH3:35])[C:16](=[O:34])[C:17]([C:20]2[CH:21]=[C:22]([C:30]([F:31])([F:32])[F:33])[CH:23]=[C:24]([C:26]([F:29])([F:27])[F:28])[CH:25]=2)([CH3:19])[CH3:18])=[C:11]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=2[CH3:42])[CH:10]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 9808492HCID 9808492, compound

Product 1

HCID 9913704HCID 9913704, compoundYield 81%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

A solution of 750 mg (1.28 mmol) N-(6-benzylamino-4-o-tolyl-pyridin-3-yl)-2-(3,5-bis-trifluoromethyl-phenyl)-N-methyl-isobutyramide (Example 73, step d) in 25 ml of a 5 N solution of hydrochloric acid in ethanol was evaporated to dryness and the residue was dissolved in 30 ml methanol and hydrogenated in the presence of 60 mg 10% palladium on activated charcoal (room temperature, 10 bar) for 20 h. After filtration of the catalyst and evaporation of the solvent the residue was dissolved in 30 ml ethyl acetate, washed twice with saturated aqueous sodium hydrogencarbonate solution and dried (magnesium sulfate). Evaporation of the solution afforded 514 mg (81%) of the title compound as light brown crystals.

Workup

  1. filtrationAfter filtration of the catalyst and evaporation of the solvent the residue
  2. dissolutionwas dissolved in 30 ml ethyl acetate
  3. washwashed twice with saturated aqueous sodium hydrogencarbonate solution
  4. dry with materialdried (magnesium sulfate)
  5. customEvaporation of the solution

Sources & evidence

ORD record
ord-f18932bceb244db489c415f89cb14f40
Source dataset
uspto-grants-2001_10
Patent number
US06297375B1

Reaction notes

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