Water → N-[6-(1-tert-butyloxycarbonylpiperidin-4-yl)-5-methylpyridin-3-yl]-5-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamide

HRID 1748590Notes

Reaction equation

HRID 1748590 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:19]([CH3:20])=[CH:18][C:17]([NH2:21])=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:22][C:23]1[N:27]([C:28]2[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][N:29]=2)[N:26]=[CH:25][C:24]=1[C:38](Cl)=[O:39].C(N(CC)CC)C.O>N1C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[N:15]=[CH:16][C:17]([NH:21][C:38]([C:24]3[CH:25]=[N:26][N:27]([C:28]4[CH:33]=[CH:32][C:31]([C:34]([F:36])([F:37])[F:35])=[CH:30][N:29]=4)[C:23]=3[CH3:22])=[O:39])=[CH:18][C:19]=2[CH3:20])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 866925404-(5-Amino-3-methylpyridin-2-yl)piperidine-1-carboxylic acid tert-butyl esterHCID 897349975-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid chloride

Product 1

HCID 86692542N-[6-(1-tert-butyloxycarbonylpiperidin-4-yl)-5-methylpyridin-3-yl]-5-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamideYield 85.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 4-(5-amino-3-methylpyridin-2-yl)piperidine-1-carboxylic acid tert-butyl ester (4.4 g) in pyridine (50 ml) was added 5-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid chloride (5.16 g) described in Reference Example 180 at 0° C., and stirred at room temperature for 1 hour. To the reaction solution was added triethylamine (6.33 ml), then water was added thereto, and the precipitated solid was washed with water and ethyl acetate to give N-[6-(1-tert-butyloxycarbonylpiperidin-4-yl)-5-methylpyridin-3-yl]-5-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamide (7.0 g) as a pale yellow solid.

Workup

  1. customdescribed in Reference Example 180 at 0° C.
  2. washthe precipitated solid was washed with water and ethyl acetate

Sources & evidence

ORD record
ord-7a5a29e7b6f540288529b4e39bff47d9
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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