5-Aminoisoquinoline → N-5-isoquinolinyl-3-[4-(trifluoromethyl)phenyl]acrylamide

HRID 586054Notes

Reaction equation

HRID 586054 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2.[F:12][C:13]([F:26])([F:25])[C:14]1[CH:19]=[CH:18][C:17]([CH:20]=[CH:21][C:22](O)=[O:23])=[CH:16][CH:15]=1>CO>[CH:7]1[C:8]2[C:3](=[C:2]([NH:1][C:22](=[O:23])[CH:21]=[CH:20][C:17]3[CH:16]=[CH:15][C:14]([C:13]([F:25])([F:26])[F:12])=[CH:19][CH:18]=3)[CH:11]=[CH:10][CH:9]=2)[CH:4]=[CH:5][N:6]=1

Participants

4

Reactant 2

HCID 707665-AminoisoquinolineHCID 749403-[4-(Trifluoromethyl)phenyl]prop-2-enoic acid

Product 1

HCID 68881390N-5-isoquinolinyl-3-[4-(trifluoromethyl)phenyl]acrylamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
175 °C

Procedure

5-Aminoisoquinoline (0.50 g, 3.47 mmol) and 3-[4-(trifluoromethyl)phenyl]acrylic acid (3.47 mmol) were combined in a sealed tube and heated at 175° C. for 16 hours with stirring. The mixture was cooled to room temperature, diluted with MeOH, transferred to a flask, and concentrated under reduced pressure. The residue was triturated with ethyl acetate and filtered to provide the title compound. MS (ESI+) m/z 343 (M+H)+; MS (ESI−) m/z 341 (M−H)−; 1H NMR (DMSO, 300 MHz) rotamers δ 6.68 (d, J 15.9, 1H), 7.29 (d, J 15.9, 1H), 7.60 (d, J 15.9, 1H), 7.80 (m, 1H), 8.25 (d, J 6.8, 1H), 8.57 (d, J 5.8, 1H), 9.35 (s, 1H), 10.36 (s, 1H); Anal. Calcd for C19H13F3N2O+2 HCl+0.3H2O: C, 54.25; H, 3.74; N, 6.66. Found: C, 53.90; H, 3.94; N, 7.20.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customtransferred to a flask
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was triturated with ethyl acetate
  5. filtrationfiltered

Sources & evidence

ORD record
ord-deea5f211e5c43e79cfbe3c04a256e47
Source dataset
uspto-grants-2005_08
Patent number
US06933311B2

Reaction notes

Loading…