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

HRID 585937Notes

Reaction equation

HRID 585937 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 C17H12BrCl2N3OHCl0.25EtOH: 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-87f0ec779bd44a77837537644b9a2f69
Source dataset
uspto-grants-2005_08
Patent number
US06933311B2

Reaction notes

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