Phosphorus oxychloride → N-Isoxazol-3-Yl-4-Methyl-3-[6-(4-Methylpiperazin-1-Yl)-4-Oxo-Quinazolin-3-Yl]benzamide

HRID 641945Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 641945
P(Cl)(Cl)(Cl)=O.[CH3:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][C:8]=1[N:16]1[C:25](=[O:26])[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([N:27]3[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]3)[CH:23]=2)[N:18]=[CH:17]1.[NH2:34][C:35]1[CH:39]=[CH:38][O:37][N:36]=1>N1C=CC=CC=1>[O:37]1[CH:38]=[CH:39][C:35]([NH:34][C:11](=[O:13])[C:10]2[CH:14]=[CH:15][C:7]([CH3:6])=[C:8]([N:16]3[C:25](=[O:26])[C:24]4[C:19](=[CH:20][CH:21]=[C:22]([N:27]5[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]5)[CH:23]=4)[N:18]=[CH:17]3)[CH:9]=2)=[N:36]1

Komponenten

5

Edukt 3

HCID 24813Phosphorus oxychlorideHCID 18102163-IsoxazolamineHCID 669188194-methyl-3-[6-(4-methylpiperazin-1-yl)-4-oxoquinazolin-3(4H)-yl]benzoic acid

Produkt 1

HCID 11554076N-Isoxazol-3-Yl-4-Methyl-3-[6-(4-Methylpiperazin-1-Yl)-4-Oxo-Quinazolin-3-Yl]benzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

Phosphorus oxychloride (0.11 ml) was added to a mixture of 4-methyl-3-[6-(4-methylpiperazin-1-yl)-4-oxoquinazolin-3(4H)-yl]benzoic acid (0.30 g), 3-aminoisoxazole (0.12 ml) and pyridine (5 ml) and the resultant suspension was heated to 120° C. for 5 minutes in a microwave (Personal Chemistry Emrys Optimizer with 300 W magnetron). The mixture was evaporated. The residue was partitioned between ethyl acetate and saturated NaHCO3 solution. The organic phase was dried (magnesium sulphate), evaporated and the residue purified by column chromatography on a silica column using initially methylene chloride and then a 9:1 mixture of methylene chloride and methanol as eluent. There was thus obtained the title compound (0.14 g); NMR Spectrum: (DMSOd6) 2.19 (s, 3H), 2.24 (s, 3H), 2.49 (m, 4H), 3.29 (m, 4H), 7.06 (d, 1H), 7.50 (d, 1H), 7.63 (m, 3H), 8.09 (m, 2H), 8.13 (s, 1H), 8.85 (d, 1H), 11.46 (s, 1H); Mass Spectrum: M+H+ 445.

Aufarbeitung

  1. customThe mixture was evaporated
  2. customThe residue was partitioned between ethyl acetate and saturated NaHCO3 solution
  3. dry with materialThe organic phase was dried (magnesium sulphate)
  4. customevaporated
  5. customthe residue purified by column chromatography on a silica column
  6. additiona 9:1 mixture of methylene chloride and methanol as eluent

Quellen und Nachweise

ORD-Eintrag
ord-60e44bdf2192407ca0e9a2250f964cf4
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07696215B2

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