Toluene → N-(8-bromo-5-isoquinolinyl)-N'-(2,4-dichlorobenzyl)urea

HRID 1791307Notes

Reaction equation

HRID 1791307 reaction equation
[Br:1][C:2]1[C:11]2[CH:10]=[N:9][CH:8]=[CH:7][C:6]=2[C:5]([NH2:12])=[CH:4][CH:3]=1.C1(C)C=CC=CC=1.[Cl:20][C:21]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:22]=1[CH2:28][N:29]=[C:30]=[O:31]>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:12][C:30]([NH:29][CH2:28][C:22]2[CH:23]=[CH:24][C:25]([Cl:27])=[CH:26][C:21]=2[Cl:20])=[O:31])=[C:6]2[C:11]=1[CH:10]=[N:9][CH:8]=[CH:7]2

Participants

5

Reactant 3

HCID 1140TolueneHCID 46127082,4-Dichlorobenzyl isocyanateHCID 220326308-Bromoisoquinolin-5-amine

Product 1

HCID 10093879N-(8-bromo-5-isoquinolinyl)-N'-(2,4-dichlorobenzyl)ureaYield 80.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The product from Example 73A (120 mg, 0.52 mmol) in THF:toluene (1.4, 5 mL) was treated with a solution of 2,4-dichloro-1-(isocyanatomethyl)benzene (108 mg, 0.52 mmol) in THF (0.5 mL). After stirring for 16 hours at room temperature, the mixture was filtered and the filter cake dried under reduced pressure to provide the title compound as a white solid (178 mg, 78%). The hydrochloride salt was obtained by dissolving the product in hot THF and adding HCl in diethyl ether (2M). The yellow precipitate was collected by filtration and dried under reduced pressure. MS (ESI+) m/z 426 (M+H)+; MS (ESI−) m/z 424 (M−H)−; 1H NMR (DMSO-d6, 300 MHz) δ 4.42 (d, 5.8, 2H), 7.22 (t, J 5.8, 1H), 7.65 (m, 1H), 7.91 (d, J 8.5, 1H), 8.02 (d, J 6.1, 1H), 8.22 (d, J 8.5, 1H), 8.69 (d, J 5.8, 1H), 9.01 (s, 1H), 9.44 (s, 1H); Anal. Calcd for C17H12BrCl2N3O HCl 0.25 EtOH: C, 44.41; H, 3.14; N, 8.88. Found: C, 44.80; H, 2.76; N, 8.84.

Workup

  1. filtrationthe mixture was filtered
  2. customthe filter cake dried under reduced pressure

Sources & evidence

ORD record
ord-2dd9c98cd52743aeb03c3f220dba9b0f
Source dataset
uspto-grants-2006_07
Patent number
US07074805B2

Reaction notes

Loading…