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

HRID 585999Notes

Reaction equation

HRID 585999 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-db9150ea86aa433e8c1de95b85530479
Source dataset
uspto-grants-2005_08
Patent number
US06933311B2

Reaction notes

Loading…