Disodium disulfite → 6-fluoro-8-methyl-2-[4-(4-methyl-piperazin-1-yl)-phenyl]-3H-quinazolin-4-one

HRID 1050963Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1050963
[NH2:1][C:2]1[C:10]([CH3:11])=[CH:9][C:8]([F:12])=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[CH3:13][N:14]1[CH2:19][CH2:18][N:17]([C:20]2[CH:27]=[CH:26][C:23]([CH:24]=O)=[CH:22][CH:21]=2)[CH2:16][CH2:15]1.S(OS([O-])=O)([O-])=O.[Na+].[Na+]>CN1CCCC1=O>[F:12][C:8]1[CH:7]=[C:3]2[C:2](=[C:10]([CH3:11])[CH:9]=1)[N:1]=[C:24]([C:23]1[CH:22]=[CH:21][C:20]([N:17]3[CH2:16][CH2:15][N:14]([CH3:13])[CH2:19][CH2:18]3)=[CH:27][CH:26]=1)[NH:6][C:4]2=[O:5]

Komponenten

5

Edukt 3

HCID 24346Disodium disulfiteHCID 7365334-(4-Methylpiperazin-1-yl)benzaldehydeHCID 68276549HCID 68276549, Verbindung

Produkt 1

HCID 1362370046-fluoro-8-methyl-2-[4-(4-methyl-piperazin-1-yl)-phenyl]-3H-quinazolin-4-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

A solution of 2-amino-5-fluoro-3-methyl-benzamide (84.1 mg, 0.50 mmol), 4-(4-methyl-piperazin-1-yl)-benzaldehyde (123 mg, 0.60 mmol) and sodium disulfite (97 mg, 0.51 mmol) in N-methyl-pyrrolidone (1 ml) is heated to 150° C. and stirred at this temperature for 16 hours. The reaction mixture is allowed to reach room temperature and poured into ice water. The resulting precipitate is collected by filtration, washed with water and dried. The residue is chromatographed on a silica gel column with methanol/dichloromethane as eluent to afford 6-fluoro-8-methyl-2-[4-(4-methyl-piperazin-1-yl)-phenyl]-3H-quinazolin-4-one as brown powder; HPLC/MS 1.47 min (A), [M+H] 353; 1H NMR (400 MHz, DMSO-d6) δ [ppm] 12.34 (s, 1H), 8.69-7.90 (m, 2H), 7.86-7.26 (m, 2H), 7.28-6.73 (m, 2H), 3.33-3.27 (m, 4H), 2.61 (s, 3H), 2.45 (t, J=5.1 Hz, 4H), 2.23 (s, 3H).

Aufarbeitung

  1. customto reach room temperature
  2. filtrationThe resulting precipitate is collected by filtration
  3. washwashed with water
  4. customdried
  5. customThe residue is chromatographed on a silica gel column with methanol/dichloromethane as eluent

Quellen und Nachweise

ORD-Eintrag
ord-abafbaa13b2c43bc8b750ee31bf4775a
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09388142B2

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