Ammonia → 2-[(2-amino-pyridin-4-ylmethyl)-amino]-N-(3-trifluoromethyl-phenyl)-benzamide

HRID 858933Notes

Reaction equation

HRID 858933 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH2:8][NH:9][C:10]2[CH:28]=[CH:27][CH:26]=[CH:25][C:11]=2[C:12]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=2)=[O:13])[CH:5]=[CH:4][N:3]=1.[NH3:29]>C(O)(O)C.[Cu-]=O>[NH2:29][C:2]1[CH:7]=[C:6]([CH2:8][NH:9][C:10]2[CH:28]=[CH:27][CH:26]=[CH:25][C:11]=2[C:12]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=2)=[O:13])[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 103437292-[(2-bromo-pyridin-4-ylmethyl)-amino]-N-(3-trifluoromethyl-phenyl)-benzamide

Product 1

HCID 121352662-[(2-amino-pyridin-4-ylmethyl)-amino]-N-(3-trifluoromethyl-phenyl)-benzamideYield 51%

Reagents, catalysts & solvents 2

HCID 178419072HCID 178419072, compoundCatalystHCID 1512111,1-EthanediolSolvent

Procedure

8.747 g (19.4 mmol) of 2-[(2-bromo-pyridin-4-ylmethyl)-amino]-N-(3-trifluoromethyl-phenyl)-benzamide is heated with 175 mg of copper(I) oxide in 150 ml of ethanediol for 23 hours under 10 bar of ammonia pressure to 80° C. in an autoclave. After the solvent is distilled off in a vacuum, the residue is purified on silica gel with a gradient of ethyl acetate:ethanol=100:0 to 0:100 as an eluant. 4.15 g (51% of theory) of 2-[(2-amino-pyridin-4-ylmethyl)-amino]-N-(3-trifluoromethyl-phenyl)-benzamide with a melting point of 64° C. is obtained.

Workup

  1. distillationAfter the solvent is distilled off in a vacuum
  2. customthe residue is purified on silica gel with a gradient of ethyl acetate

Sources & evidence

ORD record
ord-d3ef42709a09458693b9a18c10a80dfc
Source dataset
uspto-grants-2006_12
Patent number
US07148357B2

Reaction notes

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