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

HRID 629062

반응식

HRID 629062 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-558cfcfaa1894890bfcc2b5f9ea3663c
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09315489B2

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