2-Pyridinemethanamine → HCID 178446324, compound

HRID 1471442Notes

Reaction equation

HRID 1471442 reaction equation
C(O/[C:4](=[C:9]1/[C:10]([CH2:16][C:17]([O:19][CH3:20])=[O:18])=[N:11][N:12]([CH3:15])[C:13]/1=[O:14])/[CH2:5][CH2:6][CH2:7][CH3:8])C.[N:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH2:27][NH2:28]>C1(C)C=CC=CC=1>[CH3:15][N:12]1[C:13](=[O:14])/[C:9](=[C:4](\[NH:28][CH2:27][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][N:21]=2)/[CH2:5][CH2:6][CH2:7][CH3:8])/[C:10]([CH2:16][C:17]([O:19][CH3:20])=[O:18])=[N:11]1

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-95096ed1196f4f92bf223094385b6641
Source dataset
uspto-grants-2015_04
Patent number
US09012449B2

Reaction notes

Loading…