Methyl 6-formylpyridine-3-carboxylate → methyl 6-((5-methyl-6-(4-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-3-ylimino)methyl)nicotinate

HRID 537537

Reaction equation

HRID 537537 reaction equation
[CH:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][N:4]=1)=O.[CH3:13][C:14]1[CH:15]=[C:16]([NH2:29])[CH:17]=[N:18][C:19]=1[N:20]1[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[N:21]1>C1(C)C=CC=CC=1>[CH3:13][C:14]1[CH:15]=[C:16]([N:29]=[CH:1][C:3]2[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][N:4]=2)[CH:17]=[N:18][C:19]=1[N:20]1[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[N:21]1

Participants

4

Reactant 2

HCID 586269Methyl 6-formylpyridine-3-carboxylateHCID 641737255-methyl-6-(4-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-3-amine

Product 1

HCID 68156512methyl 6-((5-methyl-6-(4-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-3-ylimino)methyl)nicotinateYield 100%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of methyl 6-formylnicotinate (251.3 mg, 1.52 mmol) and 5-methyl-6-(4-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-3-amine (369 mg, 1.52 mmol) in toluene (8 mL) was heated at reflux under nitrogen overnight. The reaction mixture was concentrated to give methyl 6-((5-methyl-6-(4-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-3-ylimino)methyl)nicotinate (592 mg, 100%). 1H NMR (400 MHz, (CD3)2SO, δ): 9.09 (d, 1H), 8.83 (s, 1H), 8.72 (s, 1H), 8.35-8.30 (m, 2H), 8.20-8.17 (m, 1H), 8.11 (s, 1H), 7.90 (d, 1H), 3.79 (s, 3H), 2.32 (s, 3H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen overnight
  3. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-f154fc37cebd44cbbc79d4bfba10ec83
Source dataset
uspto-grants-2014_10
Patent number
US08859591B2

Linked notes

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