Dichloromethane → N-{3-[3-(4-methylpiperazin-1-ylmethyl)benzamido]-4-methylphenyl}dibenzofuran-4-carboxamide

HRID 1281733

Reaktionsgleichung

Reaktionsgleichung von HRID 1281733
C(N(C(C)C)CC)(C)C.[NH2:10][C:11]1[CH:12]=[CH:13][C:14]([CH2:34]C)=[C:15]([NH:17][C:18](=[O:33])[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][N:26]3[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][CH2:27]3)[CH:20]=2)[CH:16]=1.[CH:36]1[C:44]2[C:43]3[CH:45]=[CH:46][CH:47]=[CH:48][C:42]=3[O:41][C:40]=2[C:39]([C:49]([OH:51])=O)=[CH:38][CH:37]=1.C(Cl)Cl>CC(C)=O>[CH3:32][N:29]1[CH2:30][CH2:31][N:26]([CH2:25][C:21]2[CH:20]=[C:19]([CH:24]=[CH:23][CH:22]=2)[C:18]([NH:17][C:15]2[CH:16]=[C:11]([NH:10][C:49]([C:39]3[C:40]4[O:41][C:42]5[CH:48]=[CH:47][CH:46]=[CH:45][C:43]=5[C:44]=4[CH:36]=[CH:37][CH:38]=3)=[O:51])[CH:12]=[CH:13][C:14]=2[CH3:34])=[O:33])[CH2:27][CH2:28]1

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 81531DiisopropylethylamineHCID 3028728-Oxatricyclo(7.4.0.0,2,7)trideca-1(9),2(7),3,5,10,12-hexaene-6-carboxylic acidHCID 18422068N-(5-amino-2-ethylphenyl)-3-(4-methylpiperazin-1-ylmethyl)benzamide

Produkt 1

HCID 9936896N-{3-[3-(4-methylpiperazin-1-ylmethyl)benzamido]-4-methylphenyl}dibenzofuran-4-carboxamideAusbeute 54,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

Diisopropylethylamine (0.4 ml) was added to a stirred mixture of N-(5-amino-2-ethylphenyl)-3-(4-methylpiperazin-1-ylmethyl)benzamide (0.2 g), dibenzofuran-4-carboxylic acid (0.133 g), 2-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate(V) (0.22 g) and methylene chloride (10 ml) and the mixture was stirred at ambient temperature for 16 hours. The mixture was evaporated and the residue was partitioned between methylene chloride and a saturated aqueous sodium bicarbonate solution. The organic phase was dried over magnesium sulphate and evaporated. The residue was purified by column chromatography on silica using increasingly polar mixtures of methylene chloride and methanol as eluent. The material so obtained was dissolved in acetone and reprecipitated by the addition of isohexane. There was thus obtained the title compound (0.164 g); NMR Spectrum: (DMSOd6) 1.15 (t, 3H), 2.25 (s, 3H), 2.35-2.5 (m, 8H), 2.6 (m, 2H), 3.55 (s, 2H), 7.3 (d, 1H), 7.4-7.6 (m, 5H), 7.65 (m, 1H), 7.8-7.9 (m, 5H), 8.2 (d, 1H), 8.35 (d, 1H), 9.95 (s, 1H), 10.43 (s, 1H); Mass Spectrum: M+H+ 547.

Aufarbeitung

  1. customThe mixture was evaporated
  2. customthe residue was partitioned between methylene chloride
  3. dry with materialThe organic phase was dried over magnesium sulphate
  4. customevaporated
  5. customThe residue was purified by column chromatography on silica using
  6. temperatureincreasingly polar mixtures of methylene chloride and methanol as eluent
  7. customThe material so obtained
  8. customreprecipitated by the addition of isohexane

Quellen und Nachweise

ORD-Eintrag
ord-e81edc5f94a94a6eb4cfa8814e3d5d85
Quelldatensatz
uspto-grants-2002_09
Patentnummer
US06455520B1

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