Potassium Carbonate → HCID 86598044, compound

HRID 1181489Notes

Reaction equation

HRID 1181489 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[C:12]2[CH:11]=[N:10][CH:9]=[CH:8][C:7]=2[C:6]([NH2:13])=[CH:5][CH:4]=1.[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.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[F:15][C:2]([F:1])([F:14])[C:3]1[CH:4]=[CH:5][C:6]([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:7]2[C:12]=1[CH:11]=[N:10][CH:9]=[CH:8]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 223376994-(Trifluoromethyl)benzyl isocyanate3×HCID 69523481HCID 69523481, compound2×

Product 1

HCID 86598044HCID 86598044, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 8-(trifluoromethyl)isoquinolin-5-amine (Description 93; 150 mg, 0.708 mmol) in CDCl3 (10 ml) was added [4-(trifiuoromethyl)benzyl]isocyanate (Description 58) [0.506M soln in DCM; 1.403 ml, 0.71 mmol) and the resulting mixture heated at reflux overnight. NMR analysis showed a deficit of the [4-(trifluoromethyl)benzyl]isocyanate in comparison to remaining 8-(trifluoromethyl)isoquinolin-5-amine so a further portion of [4-(trifluoromethyl)benzyl]isocyanate [0.506M solution in DCM] (1.403 ml; 0.71 mmol) was added and refluxing continued for 2 days. The cooled reaction mixture was evaporated to dryness and purified by column chromatography on silica elution with 1% MeOH in DCM+0.5% NH4OH. NMR showed the product was the bis acylated urea. This material was dissolved in methanol (5 ml) and K2CO3 (500 mg, 3.6 mmol) added and the mixture stirred at room temperature for 2.5 hours. The mixture was filtered and the residue purified by preparative TLC eluting with 10% MeOH in DCM+0.5% NH4OH to give the title compound (100 mg, 34%) as a white solid. m/z (ES+) 414 (M+H)+.

Workup

  1. temperature1.403 ml, 0.71 mmol) and the resulting mixture heated
  2. temperatureat reflux overnight
  3. additionwas added
  4. temperaturerefluxing
  5. customThe cooled reaction mixture
  6. customwas evaporated to dryness
  7. custompurified by column chromatography on silica elution with 1% MeOH in DCM+0.5% NH4OH
  8. dissolutionThis material was dissolved in methanol (5 ml)
  9. filtrationThe mixture was filtered
  10. customthe residue purified by preparative TLC
  11. washeluting with 10% MeOH in DCM+0.5% NH4OH

Sources & evidence

ORD record
ord-fd97c1a70d074b5a9cb5e16b78b1af07
Source dataset
uspto-grants-2007_10
Patent number
US07285563B2

Reaction notes

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