4-(Trifluoromethyl)benzyl isocyanate → HCID 69522969, compound

HRID 1181499Notes

Reaction equation

HRID 1181499 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([CH2:12][CH2:13][NH:14]C(=O)OC(C)(C)C)[N:6]=[CH:7]2.[F:22][C:23]([F:35])([F:34])[C:24]1[CH:33]=[CH:32][C:27]([CH2:28][N:29]=[C:30]=[O:31])=[CH:26][CH:25]=1>>[NH2:14][CH2:13][CH2:12][C:5]1[N:6]=[CH:7][C:8]2[C:3]([CH:4]=1)=[C:2]([NH:1][C:30]([NH:29][CH2:28][C:27]1[CH:26]=[CH:25][C:24]([C:23]([F:22])([F:35])[F:34])=[CH:33][CH:32]=1)=[O:31])[CH:11]=[CH:10][CH:9]=2

Participants

3

Reactant 2

HCID 223376994-(Trifluoromethyl)benzyl isocyanateHCID 69522826HCID 69522826, compound

Product 1

HCID 69522969HCID 69522969, compoundYield 9.2%

Procedure

To a solution of tert-butyl 2-(5-aminoisoquinolin-3-yl)ethylcarbamate (Description 116; 200 mg, 0.7 mmol) in deuterated chloroform (5 ml) was added [4-(trifluoromethyl)benzyl]isocyanate (0.506M solution in DCM) (Description 58; 1.38 ml, 0.7 mmol), and the resulting mixture heated at reflux overnight. The reaction mixture was cooled and the precipitate removed by filtration, washed with DCM and dried. The solid was dissolved in methanol (10 ml) and hydrogen chloride gas passed through the mixture for 5 mins, after which time the mixture was left standing for 1 hour. The mixture was evaporated and purified using an SCX cartridge—appropriate fractions were evaporated to give the title compound (25 mg, 9%) as a white solid. m/z (ES+) 389 (M+H)+.

Workup

  1. temperaturethe resulting mixture heated
  2. temperatureat reflux overnight
  3. temperatureThe reaction mixture was cooled
  4. customthe precipitate removed by filtration
  5. washwashed with DCM
  6. customdried
  7. dissolutionThe solid was dissolved in methanol (10 ml)
  8. waitafter which time the mixture was left
  9. waitstanding for 1 hour
  10. customThe mixture was evaporated
  11. custompurified
  12. customwere evaporated

Sources & evidence

ORD record
ord-d1cb4aca4f0d4b46945ec42d868bd6e5
Source dataset
uspto-grants-2007_10
Patent number
US07285563B2

Reaction notes

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