trans-2-Phenylcyclopropyl isocyanate → 1-[6-methoxy-7-(N-methylpiperidin-4-ylmethoxy)quinazolin-4-yl]-3-(trans-2-phenylcyclopropyl)urea

HRID 393239

Reaktionsgleichung

Reaktionsgleichung von HRID 393239
[C:1]1([C@@H:7]2[CH2:9][C@H:8]2[N:10]=[C:11]=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:13][C:14]1[C:23]2[C:18](=[CH:19][C:20]([O:26][CH2:27][CH:28]3[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]3)=[C:21]([O:24][CH3:25])[CH:22]=2)[N:17]=[CH:16][N:15]=1>C(Cl)(Cl)Cl>[CH3:25][O:24][C:21]1[CH:22]=[C:23]2[C:18](=[CH:19][C:20]=1[O:26][CH2:27][CH:28]1[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]1)[N:17]=[CH:16][N:15]=[C:14]2[NH:13][C:11]([NH:10][C@@H:8]1[CH2:9][C@H:7]1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:12]

Komponenten

4

Edukt 2

HCID 255285trans-2-Phenylcyclopropyl isocyanateHCID 222439084-amino-6-methoxy-7-(N-methylpiperidin-4-ylmethoxy)quinazoline

Produkt 1

HCID 694638691-[6-methoxy-7-(N-methylpiperidin-4-ylmethoxy)quinazolin-4-yl]-3-(trans-2-phenylcyclopropyl)urea

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel2×

Versuchsvorschrift

trans-2-Phenylcyclopropyl isocyanate (0.2 ml) was added to a stirred mixture of 4-amino-6-methoxy-7-(1-methylpiperidin-4-ylmethoxy)quinazoline (0.1 g) and chloroform (3 ml) and the resultant mixture was stirred at ambient temperature for 20 hours. The reaction mixture was diluted with chloroform (3 ml) and tris-(2-aminoethyl)amine polystyrene resin (0.5 g) was added. The mixture was stirred at ambient temperature for 1 hour. The mixture was filtered and the filtrate was evaporated. The residue was purified by column chromatography, on silica using increasingly polar mixtures of methylene chloride and 2M methanolic ammonia as eluent. There was thus obtained the title compound (0.11 g); NMR Spectrum: (CDCl3) 1.24-1.38 (m, 2H), 1.41-1.57 (m, 2H), 1.87-2.05 (m, 5H), 2.21 (m, 1H), 2.3 (s, 3H), 2.91 (d, 2H), 3.05 (m, 1H), 3.97 (s, 3H), 4.04 (d, 2H), 7.1-7.26 (m, 6H partially obscured by CHCl3 peak), 7.34 (m, 1H), 8.66 (s, 1H), 8.72 (s, 1H), 10.31 (s, 1H); Mass Spectrum: M+H+ 462.

Aufarbeitung

  1. additionwas added
  2. filtrationThe mixture was filtered
  3. customthe filtrate was evaporated
  4. customThe residue was purified by column chromatography, on silica using
  5. temperatureincreasingly polar mixtures of methylene chloride and 2M methanolic ammonia as eluent

Quellen und Nachweise

ORD-Eintrag
ord-5a4b1be83ee543cbb14511700a4901da
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06806274B1

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