2-Pyridinemethanamine → HCID 178499640, compound

HRID 447891Notes

Reaction equation

HRID 447891 reaction equation
[CH3:1][O:2][C:3](=[O:23])[CH2:4][C:5]1=[N:6][N:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:22])[C:8](=[O:15])/[C:9]/1=[C:10](/OCC)\[CH3:11].[N:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH2:30][NH2:31]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:23])[CH2:4][C:5]1=[N:6][N:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:22])[C:8](=[O:15])/[C:9]/1=[C:10](/[NH:31][CH2:30][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][N:24]=1)\[CH3:11]

Participants

4

Reactant 2

HCID 195092-PyridinemethanamineHCID 86701218methyl [(4E)-1-(2-chlorophenyl)-4-(1-ethoxyethylidene)-5-oxo-4,5-dihydro-1H-pyrazol-3-yl]acetate

Product 1

HCID 178499640HCID 178499640, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The mixture of the above obtained methyl[(4E)-1-(2-chlorophenyl)-4-(1-ethoxyethylidene)-5-oxo-4,5-dihydro-1H-pyrazol-3-yl]acetate (Compound of Formula (VII), 1.26 g) and 1-pyridin-2-ylmethanamine (0.262 mL) was stirred at room temperature in toluene (25 mL) for 0.5 h. The solvent was removed in vacuo. The resulting residue was dissolved in a minimum of CH2Cl2 and added dropwise to a stirred solution of 200 mL of cyclohexane resulting in the formation of a brown precipitate that was filtered off. This precipitate was proved to be the pure methyl[(4E)-1-(2-chlorophenyl)-5-oxo-4-{1-[(pyridin-2-ylmethyl)amino]ethylidene}-4,5-dihydro-1H-pyrazol-3-yl]acetate (1.42 g). Yield 95%. MS (ESI+): 399.9; MS (ESI−): 397.8.

Workup

  1. additionThe mixture of the
  2. customThe solvent was removed in vacuo
  3. dissolutionThe resulting residue was dissolved in a minimum of CH2Cl2
  4. additionadded dropwise to a stirred solution of 200 mL of cyclohexane resulting in the formation of a brown precipitate that
  5. filtrationwas filtered off

Sources & evidence

ORD record
ord-354be9bf82c3486b90054951e6eff8bf
Source dataset
uspto-grants-2013_07
Patent number
US08481562B2

Reaction notes

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