Toluene → 4-(4-Chloro-2-fluoroanilino)-6-methoxy-7-(2-(methylamino)ethoxy)quinazoline hydrochloride hydrate

HRID 1384603Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1384603
C(O)(C(F)(F)F)=[O:2].[Cl:8][C:9]1[CH:39]=[CH:38][C:12]([NH:13][C:14]2[C:23]3[C:18](=[CH:19][C:20]([O:26][CH2:27][CH2:28][N:29](C)[C:30](OC(C)(C)C)=O)=[C:21]([O:24][CH3:25])[CH:22]=3)[N:17]=[CH:16][N:15]=2)=[C:11]([F:40])[CH:10]=1.C1(C)C=CC=CC=1>C(Cl)Cl>[OH2:2].[ClH:8].[Cl:8][C:9]1[CH:39]=[CH:38][C:12]([NH:13][C:14]2[C:23]3[C:18](=[CH:19][C:20]([O:26][CH2:27][CH2:28][NH:29][CH3:30])=[C:21]([O:24][CH3:25])[CH:22]=3)[N:17]=[CH:16][N:15]=2)=[C:11]([F:40])[CH:10]=1

Komponenten

5

Edukt 3

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 226250154-(4-chloro-2-fluoroanilino)-6-methoxy-7-(2-(N-methyl-N-t-butoxycarbonylamino)ethoxy)quinazoline

Produkt 1

HCID 226249694-(4-Chloro-2-fluoroanilino)-6-methoxy-7-(2-(methylamino)ethoxy)quinazoline hydrochloride hydrateAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

TFA (4 ml) was added to a solution of 4-(4-chloro-2-fluoroanilino)-6-methoxy-7-(2-(N-methyl-N-t-butoxycarbonylamino)ethoxy)quinazoline (390 mg, 0.82 mmol) in methylene chloride (4 ml) and the mixture stirred for 2 hours at ambient temperature. Toluene was added and the volatiles were removed by evaporation. The residue was dissolved in methylene chloride and 3M ethereal hydrogen chloride (1 ml) was added. The resulting precipitate was collected by filtration, washed with ether and dried under vacuum to give 4-(4-chloro-2-fluoroanilino)-6-methoxy-7-(2-(methylamino)ethoxy)quinazoline hydrochloride hydrate (290 mg; 79%). 1H NMR Spectrum: (DMSOd6; CF3COOD) 2.74(s, 3H); 3.53(t, 2H); 4.05(s, 3H); 4.53(t, 2H); 7.46(d, 1H); 7.47(s, 1H); 7.6-7.7(m, 2H); 8.24(s, 1H); 8.91(s, 1H) MS-ESI: 377 [MH]+

Aufarbeitung

  1. customthe volatiles were removed by evaporation
  2. dissolutionThe residue was dissolved in methylene chloride
  3. addition3M ethereal hydrogen chloride (1 ml) was added
  4. filtrationThe resulting precipitate was collected by filtration
  5. washwashed with ether
  6. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-e4c7fef4f2b6422495bc38e765d21b5d
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06258951B1

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