3-Pyrimidin-5-yl-benzoic acid → 3-(Pyrimidin-5-yl)-N-(4-(2,2,2-trifluoroethyl)phenyl)benzamide

HRID 629062Notes

Reaction equation

HRID 629062 reaction equation
[N:1]1[CH:6]=[C:5]([C:7]2[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=2)[C:10]([OH:12])=O)[CH:4]=[N:3][CH:2]=1.[F:16][C:17]([F:27])([F:26])[CH2:18][C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=1>C(Cl)Cl>[N:3]1[CH:4]=[C:5]([C:7]2[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=2)[C:10]([NH:23][C:22]2[CH:24]=[CH:25][C:19]([CH2:18][C:17]([F:16])([F:26])[F:27])=[CH:20][CH:21]=2)=[O:12])[CH:6]=[N:1][CH:2]=1

Participants

4

Reactant 2

HCID 41872503-Pyrimidin-5-yl-benzoic acidHCID 148368584-(2,2,2-Trifluoroethyl)aniline

Product 1

HCID 722030113-(Pyrimidin-5-yl)-N-(4-(2,2,2-trifluoroethyl)phenyl)benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-pyrimidin-5-yl-benzoic acid (100 mg, 0.50 mmol) SOCl2 (73 μL, 1.0 mmol) was heated under reflux for 4 h. The solvent was evaporated off under reduced pressure and the residue was dissolved in DCM (5 mL) and slowly added to a mixture of 4-(2,2,2-trifluoroethyl)aniline (105 mg, 0.60 mmol) and TEA (140 μL, 1.0 mmol) in DCM (5 mL). The mixture was stirred at RT overnight. The solvent was evaporated off under reduced pressure and the residue was suspended in water (20 mL) filtered and dried under vacuum to afford the title compound. LC-MS (Condition 4) tR=1.05 min, m/z=375.8 [M+H]+; 1H-NMR (400 MHz, CDCl3) δ ppm 3.40 (q, J=10.76 Hz, 2H) 7.35 (d, J=8.56 Hz, 2H) 7.65-7.71 (m, 3H) 7.80 (d, J=7.82 Hz, 1H) 7.87-7.98 (m, 2H) 8.15 (s, 1H) 9.03 (s, 2H) 9.28 (s, 1H).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 h
  3. customThe solvent was evaporated off under reduced pressure
  4. dissolutionthe residue was dissolved in DCM (5 mL)
  5. customThe solvent was evaporated off under reduced pressure
  6. filtrationfiltered
  7. customdried under vacuum

Sources & evidence

ORD record
ord-558cfcfaa1894890bfcc2b5f9ea3663c
Source dataset
uspto-grants-2016_04
Patent number
US09315489B2

Reaction notes

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