Benzyl isocyanate → 1-Benzyl-3-(isoquinolin-6-yl)urea

HRID 1807476Notes

Reaction equation

HRID 1807476 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[N:7][CH:6]=[CH:5]2.[CH2:12]([N:19]=[C:20]=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])(O)=O.[Na+]>CN(C=O)C.CN(C1C=CN=CC=1)C>[CH2:12]([NH:19][C:20]([NH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[N:7][CH:6]=[CH:5]2)=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 76639Benzyl isocyanateHCID 516892Sodium BicarbonateHCID 5889916-Aminoisoquinoline

Product 1

HCID 442769611-Benzyl-3-(isoquinolin-6-yl)urea

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To 6-aminoisoquinoline in DMF is added DMAP and benzyl isocyanate and the solution was stirred at room temperature for 4 hours. The mixture was poured into NaHCO3 (sat), extracted with EtOAc, dried (Na2SO4), filtered and evaporated. Flash chromatography (SiO2, 5% MeOH/CH2Cl2) provided 1-benzyl-3-(isoquinolin-6-yl)urea (E88).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-43f4e05db4c341eb82623371316164d9
Source dataset
uspto-grants-2013_01
Patent number
US08357699B2

Reaction notes

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