4-Bromobenzyl isocyanate → N-[(4-bromophenyl)methyl]-N'-(3-methylisoquinolin-5-yl)urea

HRID 585920

Reaktionsgleichung

Reaktionsgleichung von HRID 585920
[CH3:1][C:2]1[N:3]=[CH:4][C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([NH2:12])[C:10]=2[CH:11]=1.[Br:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][N:21]=[C:22]=[O:23])=[CH:16][CH:15]=1>C1(C)C=CC=CC=1>[Br:13][C:14]1[CH:15]=[CH:16][C:17]([CH2:20][NH:21][C:22]([NH:12][C:9]2[CH:8]=[CH:7][CH:6]=[C:5]3[C:10]=2[CH:11]=[C:2]([CH3:1])[N:3]=[CH:4]3)=[O:23])=[CH:18][CH:19]=1

Komponenten

4

Edukt 2

HCID 43746174-Bromobenzyl isocyanateHCID 122120553-Methylisoquinolin-5-amine

Produkt 1

HCID 10044630N-[(4-bromophenyl)methyl]-N'-(3-methylisoquinolin-5-yl)urea

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

The product from Example 63A (500 mg, 3.1 mmol) in toluene (10 mL) was treated with l-bromo-4-(isocyanatomethyl)benzene (0.5 mL, 3.57 mmol) with stirring and then the mixture was heated at 80° C. overnight. The mixture was allowed to cool to room temperature, filtered, the filter cake was washed with toluene, and allowed to air-dry to provide the title compound. The corresponding hydrochloride salt was prepared using methanolic HCl to afford a tan solid (919 mg, 73%). 1H NMR (300 MHz, DMSO-d6) δ 9.70 (s, 1H), 9.54 (s, 1H), 8.63 (s, 1H), 8.57 (dd, J=7.8 Hz, 1.0 Hz, 1H), 8.02 (d, J=8.2 Hz, 1H), 7.78-7.83 (m, 1H), 7.67-7.71 (m, 1H), 7.52-7.57 (m, 2H), 7.30-7.35 (m, 2H), 4.36 (d, J=5.7 Hz, 2H), 2.78 (s, 3H); MS (ESI+) m/z 370/372 (M+H, 79Br/81Br).

Aufarbeitung

  1. temperatureto cool to room temperature
  2. filtrationfiltered
  3. washthe filter cake was washed with toluene
  4. customto air-dry

Quellen und Nachweise

ORD-Eintrag
ord-2e210aecae3445fcbf543756b62d3346
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06933311B2

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