N-{6-[1-Acetyl-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-Acetylpiperidin-4-yl)-5-methylpyridin-3-yl]-5-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamide

HRID 1748670Notes

Reaction equation

HRID 1748670 reaction equation
[C:1]([N:4]1[CH2:9][CH:8]=[C:7]([C:10]2[N:15]=[CH:14][C:13]([NH:16][C:17]([C:19]3[CH:20]=[N:21][N:22]([C:25]4[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][N:26]=4)[C:23]=3[CH3:24])=[O:18])=[CH:12][C:11]=2[CH3:35])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]>O1CCOCC1.C(O)C.[C].[Pd]>[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]2[N:15]=[CH:14][C:13]([NH:16][C:17]([C:19]3[CH:20]=[N:21][N:22]([C:25]4[CH:30]=[CH:29][C:28]([C:31]([F:33])([F:34])[F:32])=[CH:27][N:26]=4)[C:23]=3[CH3:24])=[O:18])=[CH:12][C:11]=2[CH3:35])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 1

HCID 86692613N-{6-[1-Acetyl-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 86692616N-[6-(1-Acetylpiperidin-4-yl)-5-methylpyridin-3-yl]-5-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamideYield 54.2%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

N-{6-[1-Acetyl-1,2,3,6-tetrahydropyridin-4-yl]-5-methylpyridin-3-yl}-5-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamide (180 mg) described in Example K39 was dissolved in 1,4-dioxane (2 ml) and ethanol (2 ml), 10% palladium-carbon (containing ca. 50% water; 90 mg) was added, and stirred at room temperature under hydrogen atmosphere for 8.5 hours, then ethanol (1 ml) was added and stirred at 40° C. for two days. The reaction solution was filtered through Celite, washed with chloroform and ethanol and the solvent was evaporated in vacuo. The precipitated solid was washed with ethyl acetate and ethanol to give the titled compound (98 mg) as a white solid.

Workup

  1. stirringstirred at 40° C. for two days
  2. filtrationThe reaction solution was filtered through Celite
  3. washwashed with chloroform and ethanol
  4. customthe solvent was evaporated in vacuo
  5. washThe precipitated solid was washed with ethyl acetate and ethanol

Sources & evidence

ORD record
ord-8f38099d16d54f6980db210d5f718e6a
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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