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Pyridine → 5-Methyl-N-{5-methyl-6-[1-(2-methylpropanoyl)piperidin-4-yl]pyridin-3-yl}-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamide

HRID 1748682
Notes
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Reaction equation

HRID 1748682 reaction equation
[CH3:1][CH:2]([CH3:6])[C:3](Cl)=[O:4].[CH3:7][C:8]1[N:12]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][N:14]=2)[N:11]=[CH:10][C:9]=1[C:23]([NH:25][C:26]1[CH:27]=[N:28][C:29]([CH:33]2[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]2)=[C:30]([CH3:32])[CH:31]=1)=[O:24].N1C=CC=CC=1.C(N(CC)CC)C>C(O)C.O>[CH3:7][C:8]1[N:12]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:21])([F:22])[F:20])=[CH:15][N:14]=2)[N:11]=[CH:10][C:9]=1[C:23]([NH:25][C:26]1[CH:27]=[N:28][C:29]([CH:33]2[CH2:34][CH2:35][N:36]([C:3](=[O:4])[CH:2]([CH3:6])[CH3:1])[CH2:37][CH2:38]2)=[C:30]([CH3:32])[CH:31]=1)=[O:24]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 1049PyridineHCID 8471TriethylamineHCID 62325Isobutyryl chlorideHCID 866925445-Methyl-N-[5-methyl-6-(piperidin-4-yl)pyridin-3-yl]-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamide

Product 1

HCID 866926305-Methyl-N-{5-methyl-6-[1-(2-methylpropanoyl)piperidin-4-yl]pyridin-3-yl}-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamide

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

2-Methylpropanoylchloride (79 μl) was added to a mixture of 5-methyl-N-[5-methyl-6-(piperidin-4-yl)pyridin-3-yl]-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamide (222 mg) described in Reference Example 171 and pyridine (2.5 ml), and stirred at 40° C. for five hours. Triethylamine (350 μl), water and ethanol were added to the reaction solution, and the precipitated solid was washed with water to give the titled compound (220 mg) as a white solid.

Workup

  1. washthe precipitated solid was washed with water

Sources & evidence

ORD record
ord-c7ad1d0cd07a4315a5626b736fd3f7cb
Source dataset
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09150555B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes