4-(Trifluoromethyl)benzyl isocyanate → HCID 86598045, compound

HRID 1181490Notes

Reaction equation

HRID 1181490 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:12]=[CH:11][C:10]2[CH:9]=[N:8][CH:7]=[CH:6][C:5]=2[C:4]=1[NH2:13].[F:16][C:17]([F:29])([F:28])[C:18]1[CH:27]=[CH:26][C:21]([CH2:22][N:23]=[C:24]=[O:25])=[CH:20][CH:19]=1>C1(C)C=CC=CC=1.C(Cl)Cl>[F:15][C:2]([F:1])([F:14])[C:3]1[C:4]([NH:13][C:24]([NH:23][CH2:22][C:21]2[CH:20]=[CH:19][C:18]([C:17]([F:16])([F:29])[F:28])=[CH:27][CH:26]=2)=[O:25])=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[N:8][CH:7]=[CH:6]2

Participants

5

Reactant 2

HCID 223376994-(Trifluoromethyl)benzyl isocyanate2×HCID 69522881HCID 69522881, compound

Product 1

HCID 86598045HCID 86598045, compoundYield 4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 6-(trifluoromethyl)isoquinolin-5-amine (Description 98; 100 mg, 0.47 mmol) in anhydrous toluene (5 ml) was added [4-(trifluoromethyl)benzyl]isocyanate (Description 58) [0.506M soln in DCM] (1.88 ml; 0.94 mmol) and the mixture heated at reflux overnight. Further [4-(trifluoromethyl)benzyl]isocyanate [0.506M soln in DCM] (1.88 ml; 0.94 mmol) was added and heating continued for 4 days. The toluene was removed, the residue dissolved in methanol (10 ml) and a spatula end of potassium carbonate added. The mixture was then heated at reflux for 15 mins. The mixture was cooled and filtered and the filtrate evaporated. The residue was purified by mass directed HPLC to give the title compound (8 mg, 4%) as a white solid. m/z (ES+) 414 (M+H)+.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux overnight
  3. temperatureheating
  4. customThe toluene was removed
  5. dissolutionthe residue dissolved in methanol (10 ml)
  6. additiona spatula end of potassium carbonate added
  7. temperatureThe mixture was then heated
  8. temperatureat reflux for 15 mins
  9. temperatureThe mixture was cooled
  10. filtrationfiltered
  11. customthe filtrate evaporated
  12. customThe residue was purified by mass

Sources & evidence

ORD record
ord-d75c54c770304ae1bd175a2930fd6d10
Source dataset
uspto-grants-2007_10
Patent number
US07285563B2

Reaction notes

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