Triethylamine → 5-Methyl-N-{5-methyl-1-(pyrrolidin-1-ylcarbonyl)-6-[1,2,3,6-tetrahydropyridin-4-yl]pyridin-3-yl}-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamide

HRID 1748678Notes

Reaction equation

HRID 1748678 reaction equation
C(N(CC)CC)C.[N:8]1([C:13](Cl)=[O:14])[CH2:12][CH2:11][CH2:10][CH2:9]1.[CH3:16][C:17]1[N:21]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][N:23]=2)[N:20]=[CH:19][C:18]=1[C:32]([NH:34][C:35]1[CH:36]=[N:37][C:38]([C:42]2[CH2:43][CH2:44][NH:45][CH2:46][CH:47]=2)=[C:39]([CH3:41])[CH:40]=1)=[O:33]>ClCCl.O>[CH3:16][C:17]1[N:21]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][N:23]=2)[N:20]=[CH:19][C:18]=1[C:32]([NH:34][C:35]1[CH2:36][N:37]([C:13]([N:8]2[CH2:12][CH2:11][CH2:10][CH2:9]2)=[O:14])[C:38]([C:42]2[CH2:43][CH2:44][NH:45][CH2:46][CH:47]=2)=[C:39]([CH3:41])[CH:40]=1)=[O:33]

Participants

6

Reactant 3

HCID 8471Triethylamine3×HCID 709371-Pyrrolidinecarbonyl chloride2×HCID 866925385-Methyl-N-[5-methyl-6-(1,2,3,6-tetrahydropyridin-4-yl)pyridin-3-yl]-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamide

Product 1

HCID 866926255-Methyl-N-{5-methyl-1-(pyrrolidin-1-ylcarbonyl)-6-[1,2,3,6-tetrahydropyridin-4-yl]pyridin-3-yl}-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (38 μl) and 1-pyrrolidinecarbonyl chloride (30 μl) were added to a mixture of 5-methyl-N-[5-methyl-6-(1,2,3,6-tetrahydropyridin-4-yl)pyridin-3-yl]-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamide (100 mg) described in Reference Example 170 and dichloromethane (4.6 ml), and stirred at room temperature for six hours. Then, triethylamine (380 μl) and 1-pyrrolidinecarbonyl chloride (300 μl) were added and stirred at room temperature all night and all day. Triethylamine (95 μl) and water was added to the reaction solution, dichloromethane was evaporated in vacuo, and the precipitated solid was washed with ethanol to give the titled compound (99 mg) as a pale yellow solid.

Workup

  1. stirringstirred at room temperature all night and all day
  2. customwas evaporated in vacuo
  3. washthe precipitated solid was washed with ethanol

Sources & evidence

ORD record
ord-076b0496aef04de4b30139f251fb6ab2
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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