Acetic Acid → N-{3-[(2-chloro-4-methylaminopyrimidin-5-ylmethyl)amino]-4-methylphenyl}-3-trifluoromethylbenzamide

HRID 2222248Notes

Reaction equation

HRID 2222248 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH3:9])[C:5]([CH:10]=O)=[CH:4][N:3]=1.[NH2:12][C:13]1[CH:14]=[C:15]([NH:20][C:21](=[O:32])[C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=2)[CH:16]=[CH:17][C:18]=1[CH3:19].C([BH3-])#N.[Na+].C(O)(=O)C>CO.C(Cl)(Cl)Cl>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH3:9])[C:5]([CH2:10][NH:12][C:13]2[CH:14]=[C:15]([NH:20][C:21](=[O:32])[C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:29])([F:30])[F:31])[CH:23]=3)[CH:16]=[CH:17][C:18]=2[CH3:19])=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 11529455N-(3-amino-4-methylphenyl)-3-(trifluoromethyl)benzamideHCID 722075022-Chloro-4-(methylamino)-5-pyrimidinecarboxaldehyde

Product 1

HCID 86600918N-{3-[(2-chloro-4-methylaminopyrimidin-5-ylmethyl)amino]-4-methylphenyl}-3-trifluoromethylbenzamideYield 64%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

A solution of 2-chloro-4-methylamino-pyrimidine-5-carbaldehyde (1.08 g, 6.3 mmol) and N-(3-amino-4-methyl-phenyl)-3-trifluoromethylbenzamide (2.04 g, 6.9 mmol) in MeOH (70 mL) is stirred for 2 hours at 45° C. and then treated with sodium cyanoborohydride (1.19 g, 18.9 mmol) and acetic acid (1 mL) sequentially. After stirring for 2 hours at room temperature, the reaction mixture is diluted with CHCl3 and washed with saturated NaHCO3 The organic layer is dried over MgSO4 and concentrated under reduced pressure. The residue is purified by flash column chromatography (SiO2, EtOAc/hexane=1/2) to give N-{3-[(2-chloro-4-methylaminopyrimidin-5-ylmethyl)amino]-4-methylphenyl}-3-trifluoromethylbenzamide (1.80 g, 64%) as a white solid.

Workup

  1. washwashed with saturated NaHCO3 The organic layer
  2. dry with materialis dried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe residue is purified by flash column chromatography (SiO2, EtOAc/hexane=1/2)

Sources & evidence

ORD record
ord-da4a99d7f9434c0c84cd3628f9f2af24
Source dataset
uspto-grants-2008_05
Patent number
US07371750B2

Reaction notes

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