5-Amino-1-chloroisoquinoline → N-[(4-bromophenyl)methyl]-N'-(1-chloroisoquinolin-5-yl)urea

HRID 2056808

Reaktionsgleichung

Reaktionsgleichung von HRID 2056808
[Cl:1][C:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([NH2:12])[C:6]=2[CH:5]=[CH:4][N:3]=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:7]2[CH:8]=[CH:9][CH:10]=[C:11]3[C:6]=2[CH:5]=[CH:4][N:3]=[C:2]3[Cl:1])=[O:23])=[CH:18][CH:19]=1

Komponenten

4

Edukt 2

HCID 4597715-Amino-1-chloroisoquinolineHCID 43746174-Bromobenzyl isocyanate

Produkt 1

HCID 10000490N-[(4-bromophenyl)methyl]-N'-(1-chloroisoquinolin-5-yl)ureaAusbeute 63,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

The product from Example 64A (520 mg, 2.91 mmol) in toluene (8 mL) was treated with 1-bromo-4-(isocyanatomethyl)benzene (0.41 mL, 2.93 mmol) with stirring and then the mixture was heated at 90° C. for 2 hours. The mixture was allowed to cool to room temperature, filtered, the filter cake washed with toluene, and air-dried to provide the title compound as an off-white solid (717 mg, 63%). 1H NMR (300 MHz, DMSO-d6) δ 8.89 (s, 1H), 8.34-8.37 (m, 2H), 8.00 (dd, J=6.1 Hz, 0.7 Hz, 1H), 7.92-7.95 (m, 1H), 7.73 (t, J=8.1, 1H), 7.53-7.56 (m, 2H), 7.30-7.33 (m, 2H), 7.12 (t, J=5.8Hz, 1H), 4.35 (d, J=5.8 Hz, 2H); MS (ESI+) m/z 390/392 (M+H+, 35Cl/37Cl).

Aufarbeitung

  1. temperatureto cool to room temperature
  2. filtrationfiltered
  3. washthe filter cake washed with toluene
  4. customair-dried

Quellen und Nachweise

ORD-Eintrag
ord-230420056805490da48da089ceb91b3b
Quelldatensatz
uspto-grants-2008_02
Patentnummer
US07335678B2

Verknüpfte Notizen

Wird geladen…