Triethylamine → N-(2,4-dimethyl-3-(3-(pyrimidin-4-yl)pyridin-2-yloxy)phenyl)-3-(trifluoromethyl)benzamide

HRID 446332Notes

Reaction equation

HRID 446332 reaction equation
[CH3:1][C:2]1[C:7]([O:8][C:9]2[C:14]([C:15]3[CH:20]=[CH:19][N:18]=[CH:17][N:16]=3)=[CH:13][CH:12]=[CH:11][N:10]=2)=[C:6]([CH3:21])[CH:5]=[CH:4][C:3]=1[NH2:22].[F:23][C:24]([F:35])([F:34])[C:25]1[CH:26]=[C:27]([CH:31]=[CH:32][CH:33]=1)[C:28](Cl)=[O:29].C(N(CC)CC)C>ClCCl>[CH3:1][C:2]1[C:7]([O:8][C:9]2[C:14]([C:15]3[CH:20]=[CH:19][N:18]=[CH:17][N:16]=3)=[CH:13][CH:12]=[CH:11][N:10]=2)=[C:6]([CH3:21])[CH:5]=[CH:4][C:3]=1[NH:22][C:28](=[O:29])[C:27]1[CH:31]=[CH:32][CH:33]=[C:25]([C:24]([F:23])([F:34])[F:35])[CH:26]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 752573-(Trifluoromethyl)benzoyl chlorideHCID 669703062,4-Dimethyl-3-(3-(pyrimidin-4-yl)pyridin-2-yloxy)benzenamine

Product 1

HCID 58396717N-(2,4-dimethyl-3-(3-(pyrimidin-4-yl)pyridin-2-yloxy)phenyl)-3-(trifluoromethyl)benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolved 2,4-dimethyl-3-(3-(pyrimidin-4-yl)pyridin-2-yloxy)benzenamine (100 mg, 0.342 mmol) in dichloromethane (1.0 mL), added 3-(trifluoromethyl)benzoyl chloride (107 mg, 0.513 mmol) and triethylamine (0.12 mL). Stirred at ambient temp for 4 hours and then concentrated and purified by reverse-phase HPLC (Gilson, acidic mobile phase) to yield the title compound. MS m/z=465 (M+H)+. Calc'd for C25H19F3N4O2: 464.45.

Workup

  1. concentrationconcentrated
  2. custompurified by reverse-phase HPLC (Gilson, acidic mobile phase)

Sources & evidence

ORD record
ord-b903f5ecbd3843008a982a0eea9dfe2a
Source dataset
uspto-grants-2013_07
Patent number
US08476434B2

Reaction notes

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