4-Pyridinemethanamine → N-(4-imidazolylphenyl){2-[(4-pyridylmethyl)amino](3-pyridyl)}carboxamide hydrochloride

HRID 238529Notes

Reaction equation

HRID 238529 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[NH:18][CH:19]=[CH:20][N:21]=3)=[CH:13][CH:12]=2)=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[NH2:22][CH2:23][C:24]1[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=1>>[ClH:1].[NH:21]1[CH:20]=[CH:19][N:18]=[C:17]1[C:14]1[CH:15]=[CH:16][C:11]([NH:10][C:8]([C:7]2[C:2]([NH:22][CH2:23][C:24]3[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=3)=[N:3][CH:4]=[CH:5][CH:6]=2)=[O:9])=[CH:12][CH:13]=1

Participants

3

Reactant 2

HCID 773174-PyridinemethanamineHCID 131725270HCID 131725270, compound

Product 1

HCID 131725268N-(4-imidazolylphenyl){2-[(4-pyridylmethyl)amino](3-pyridyl)}carboxamide hydrochloride

Conditions

Temperature
120 °C

Procedure

(2-Chloro-(3-pyridyl))-N-(4-imidazolylphenyl)-carboxamide was treated with 4-aminomethylpyridine (0.100 g, 0.93 mmol) and heated neat at 120° C. for 18 h. After cooling to RT, the material was purified by preparative HPLC. The final product was converted into an HCl salt by dissolution in a minimum of MeOH, treatment with an HCl ethereal solution, and evaporation of solvent. MS: (ES+) 371 (M+1)+; (ES−): 369 (M−1)−. Calc'd. for C21H18N6O—370.15.

Workup

  1. temperatureAfter cooling to RT
  2. customthe material was purified by preparative HPLC
  3. dissolutionThe final product was converted into an HCl salt by dissolution in a minimum of MeOH, treatment with an HCl ethereal solution, and evaporation of solvent

Sources & evidence

ORD record
ord-2f15a53276964e8092d407b5e23beaf3
Source dataset
uspto-grants-2014_02
Patent number
US08642624B2

Reaction notes

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