2,4-Dichlorobenzyl isocyanate → N-(2,4-dichlorobenzyl)-N'-(3-methyl-5-isoquinolinyl)urea

HRID 887276Notes

Reaction equation

HRID 887276 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([CH3:12])[N:6]=[CH:7]2.[Cl:13][C:14]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=1[CH2:21][N:22]=[C:23]=[O:24]>C1(C)C=CC=CC=1>[Cl:13][C:14]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=1[CH2:21][NH:22][C:23]([NH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([CH3:12])[N:6]=[CH:7]2)=[O:24]

Participants

4

Reactant 2

HCID 46127082,4-Dichlorobenzyl isocyanateHCID 122120553-Methylisoquinolin-5-amine

Product 1

HCID 22032612N-(2,4-dichlorobenzyl)-N'-(3-methyl-5-isoquinolinyl)urea

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5-Amino-3-methylisoquinoline (390 mg, 2.47 mmol) and the product from Example 195A (0.36 mL, 2.47 mmol) were heated in toluene (10 mL) at 80° for 2.5 hours. Upon cooling to room temperature, a precipitate formed, which was collected by filtration, washed with toluene, and air-dried. Remaining impurities were removed by slurrying the solid in 9:1 CH2Cl2:CH3OH and then filtering the mixture to provide the title compound. The corresponding hydrochloride salt was formed by treatment of the free base with methanolic HCl. 1H NMR (300 MHz, DMSO-d6) δ 9.17 (s, 1H), 8.78 (s, 1H), 8.21 (dd, 1H, J=7.4 Hz, 1.0 Hz), 7.77 (s, 1H), 7.70 (d, 1H, J=8.1 Hz), 7.64 (m, 1H), 7.44-7.52 (m, 3H), 7.14 (t, 1H, J=6.1 Hz), 4.38 (d, 2H, J=6.0 Hz), 2.65 (s, 3H); MS (ESI+) m/z 360/362 (M+H, 35Cl/37Cl).

Workup

  1. customa precipitate formed
  2. filtrationwhich was collected by filtration
  3. washwashed with toluene
  4. customair-dried
  5. customRemaining impurities were removed
  6. filtrationCH3OH and then filtering the mixture

Sources & evidence

ORD record
ord-88f75fb59c2c4f5d8ad76968c2f06d2a
Source dataset
uspto-grants-2012_08
Patent number
US08247413B2

Reaction notes

Loading…