N-{6-[1-Benzoyl-1,2,3,6-tetrahydropyridin-4-yl]-5-methylpyridin-3-yl}-5-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamide → N-[6-(1-Benzoylpiperidin-4-yl)-5-methylpyridin-3-yl]-5-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamide

HRID 1748671Notes

Reaction equation

HRID 1748671 reaction equation
[C:1]([N:9]1[CH2:14][CH:13]=[C:12]([C:15]2[N:20]=[CH:19][C:18]([NH:21][C:22]([C:24]3[CH:25]=[N:26][N:27]([C:30]4[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:32][N:31]=4)[C:28]=3[CH3:29])=[O:23])=[CH:17][C:16]=2[CH3:40])[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>O1CCOCC1.C(O)C.[C].[Pd]>[C:1]([N:9]1[CH2:14][CH2:13][CH:12]([C:15]2[N:20]=[CH:19][C:18]([NH:21][C:22]([C:24]3[CH:25]=[N:26][N:27]([C:30]4[CH:35]=[CH:34][C:33]([C:36]([F:38])([F:39])[F:37])=[CH:32][N:31]=4)[C:28]=3[CH3:29])=[O:23])=[CH:17][C:16]=2[CH3:40])[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 86692614N-{6-[1-Benzoyl-1,2,3,6-tetrahydropyridin-4-yl]-5-methylpyridin-3-yl}-5-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamide

Product 1

HCID 86692617N-[6-(1-Benzoylpiperidin-4-yl)-5-methylpyridin-3-yl]-5-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamideYield 79.7%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
40 °C

Procedure

N-{6-[1-Benzoyl-1,2,3,6-tetrahydropyridin-4-yl]-5-methylpyridin-3-yl}-5-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamide (110 mg) described in Example K40 was dissolved in 1,4-dioxane (5 ml) and ethanol (5 ml), 10% palladium-carbon (containing ca. 50% water; 90 mg) was added, and stirred at 40° C. under hydrogen atmosphere for seven hours. The reaction solution was filtered through Celite, washed with chloroform and ethanol and the solvent was evaporated in vacuo. The resulting residue was purified with silica gel chromatography (chloroform/methanol) to give the titled compound (88 mg) as a white solid.

Workup

  1. filtrationThe reaction solution was filtered through Celite
  2. washwashed with chloroform and ethanol
  3. customthe solvent was evaporated in vacuo
  4. customThe resulting residue was purified with silica gel chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-7817f4cb29cb42a389904239c0e781fd
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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