4-Bromobenzyl isocyanate → N-(4-bromobenzyl)-N'-(1,3-dimethyl-5-isoquinolinyl)urea

HRID 887267Notes

Reaction equation

HRID 887267 reaction equation
[CH3:1][C:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([NH2:12])[C:6]=2[CH:5]=[C:4]([CH3:13])[N:3]=1.[Br:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][N:22]=[C:23]=[O:24])=[CH:17][CH:16]=1>C1(C)C=CC=CC=1>[Br:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:21][NH:22][C:23]([NH:12][C:7]2[CH:8]=[CH:9][CH:10]=[C:11]3[C:6]=2[CH:5]=[C:4]([CH3:13])[N:3]=[C:2]3[CH3:1])=[O:24])=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 43746174-Bromobenzyl isocyanateHCID 223376241,3-Dimethylisoquinolin-5-amine

Product 1

HCID 11740716N-(4-bromobenzyl)-N'-(1,3-dimethyl-5-isoquinolinyl)urea

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
87.5 °C

Procedure

The product from Example 178A (375 mg, 2.2 mmol) in toluene (7 mL) was treated with 1-bromo-4-(isocyanatomethyl)benzene (0.31 mL, 2.2 mmol). After stirring at 85-90° C. for 3 hours, the mixture was cooled to room temperature and filtered. The filter cake was treated with methanolic HCl to provide the title compound as the hydrochloride salt. 1H NMR (300 MHz, DMSO-d6) δ 8.62 (s, 1H), 8.17 (d, 1H, J=7.8 Hz), 7.80 (d, 1H, J=8.5 Hz), 7.45-7.60 (m, 4H), 7.32 (d, 2H, J=8.1 Hz), 7.06 (t, 1H, 5.7 Hz), 4.34 (d, 2H, 5.8 Hz), 2.84 (s, 3H), 2.75 (s, 3H); MS (ESI+) m/z 383/385 (M+H, 79Br/81Br).

Workup

  1. temperaturethe mixture was cooled to room temperature
  2. filtrationfiltered
  3. additionThe filter cake was treated with methanolic HCl

Sources & evidence

ORD record
ord-64b1e20991bd431faa3747eedb6f8108
Source dataset
uspto-grants-2012_08
Patent number
US08247413B2

Reaction notes

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