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

HRID 629062

反応式

HRID 629062 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-558cfcfaa1894890bfcc2b5f9ea3663c
出典データセット
uspto-grants-2016_04
特許番号
US09315489B2

関連ノート

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