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

HRID 2056825Notes

Reaction equation

HRID 2056825 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.[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]>C1COCC1.C1(C)C=CC=CC=1.C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:12][C:23]([NH:22][CH2:21][C:15]2[CH:16]=[CH:17][C:18]([Cl:20])=[CH:19][C:14]=2[Cl:13])=[O:24])=[C:6]2[C:11]=1[CH:10]=[N:9][CH:8]=[CH:7]2

Participants

5

Reactant 2

HCID 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 2

HCID 8028TetrahydrofuranSolventHCID 22635083Tetrahydrofuran tolueneSolvent

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-e43b8b56ff5f4229bc8745f3c34d86e1
Source dataset
uspto-grants-2008_02
Patent number
US07335678B2

Reaction notes

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