2-Pyridinemethanamine → HCID 178446324, compound

HRID 1253449Notes

Reaction equation

HRID 1253449 reaction equation
[CH3:1][O:2][C:3](=[O:20])[CH2:4][C:5]1=[N:6][N:7]([CH3:19])[C:8](=[O:18])/[C:9]/1=[C:10](\OCC)/[CH2:11][CH2:12][CH2:13][CH3:14].[N:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH2:27][NH2:28]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:20])[CH2:4][C:5]1=[N:6][N:7]([CH3:19])[C:8](=[O:18])/[C:9]/1=[C:10](\[NH:28][CH2:27][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][N:21]=1)/[CH2:11][CH2:12][CH2:13][CH3:14]

Participants

4

Reactant 2

HCID 195092-PyridinemethanamineHCID 86686093methyl [(4Z)-4-(1-ethoxypentylidene)-1-methyl-5-oxo-4,5-dihydro-1H-pyrazol-3-yl]acetate

Product 1

HCID 178446324HCID 178446324, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The mixture of the above obtained methyl[(4Z)-4-(1-ethoxypentylidene)-1-methyl-5-oxo-4,5-dihydro-1H-pyrazol-3-yl]acetate (Compound of Formula (VII), 1.05 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[(4Z)-1-methyl-5-oxo-4-{1-[(pyridin-2-ylmethyl)amino]pentylidene}-4,5-dihydro-1H-pyrazol-3-yl]acetate (1.20 g). Yield 92%. MS (ESI+): 345.4; MS (ESI−): 342.5.

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-0c4c7b52f50b43248a71fe6f8b038445
Source dataset
uspto-grants-2013_06
Patent number
US08455485B2

Reaction notes

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