Water → HCID 71253121, Verbindung

HRID 2411458Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2411458
[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([C:9]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][C:18]=3[CH3:24])[CH2:13][CH2:12]2)=[O:10])=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[CH2:33][CH2:34][CH2:35][S:36](Cl)(=[O:38])=[O:37].O>ClCCl>[CH3:24][C:18]1[CH:19]=[C:20]([CH3:23])[CH:21]=[CH:22][C:17]=1[N:14]1[CH2:13][CH2:12][N:11]([C:9]([C:5]2[C:6]([CH3:8])=[N:7][C:2]([N:1]3[CH2:33][CH2:34][CH2:35][S:36]3(=[O:38])=[O:37])=[CH:3][CH:4]=2)=[O:10])[CH2:16][CH2:15]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 154103-Chloropropanesulphonyl chlorideHCID 71252418HCID 71252418, Verbindung

Produkt 1

HCID 71253121HCID 71253121, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

(6-Amino-2-methylpyridin-3-yl)[4-(2,4-dimethylphenyl)piperazin-1-yl]methanone (180 mg) described in Preparation Example 136 and triethylamine (0.19 mL) were dissolved in dichloromethane (5 mL), 3-chloropropane-1-sulfonyl chloride (0.14 mL) was added, and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, the mixture was extracted with dichloromethane, the extract was washed with saturated brine, and the solvent was evaporated. The obtained residue was dissolved in N,N-dimethylformamide (5 mL), 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (0.12 mL) was added, and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate, the extract was washed with saturated brine, and the solvent was evaporated. The obtained residue was purified by column chromatography (hexane:ethyl acetate) to give the title compound (57 mg).

Aufarbeitung

  1. extractionthe mixture was extracted with dichloromethane
  2. washthe extract was washed with saturated brine
  3. customthe solvent was evaporated
  4. dissolutionThe obtained residue was dissolved in N,N-dimethylformamide (5 mL)
  5. addition1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (0.12 mL) was added
  6. stirringthe mixture was stirred at room temperature overnight
  7. additionWater was added to the reaction mixture
  8. extractionthe mixture was extracted with ethyl acetate
  9. washthe extract was washed with saturated brine
  10. customthe solvent was evaporated
  11. customThe obtained residue was purified by column chromatography (hexane:ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-8f2714fb0477488587daa7b1e05a0bfb
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08816079B2

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