Acetic Acid → N-Cyclopropyl-4-methoxy-2,6-dimethyl-N-{[4-({4-[(2-methylpyridin-4-yl)methyl]piperazin-1-yl}carbonyl)-1,3-oxazol-2-yl]methyl}benzenesulfonamide

HRID 469081Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 469081
[CH:1]1([N:4]([CH2:18][C:19]2[O:20][CH:21]=[C:22]([C:24]([N:26]3[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]3)=[O:25])[N:23]=2)[S:5]([C:8]2[C:13]([CH3:14])=[CH:12][C:11]([O:15][CH3:16])=[CH:10][C:9]=2[CH3:17])(=[O:7])=[O:6])[CH2:3][CH2:2]1.[CH3:32][C:33]1[N:38]=[CH:37][CH:36]=[C:35]([CH:39]=O)[CH:34]=1.CC(O)=O>ClCCCl>[CH:1]1([N:4]([CH2:18][C:19]2[O:20][CH:21]=[C:22]([C:24]([N:26]3[CH2:31][CH2:30][N:29]([CH2:39][C:35]4[CH:36]=[CH:37][N:38]=[C:33]([CH3:32])[CH:34]=4)[CH2:28][CH2:27]3)=[O:25])[N:23]=2)[S:5]([C:8]2[C:9]([CH3:17])=[CH:10][C:11]([O:15][CH3:16])=[CH:12][C:13]=2[CH3:14])(=[O:6])=[O:7])[CH2:2][CH2:3]1

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 27630002-METHYLISONICOTINALDEHYDEHCID 58392961N-cyclopropyl-4-methoxy-2,6-dimethyl-N-{[4-(piperazin-1-ylcarbonyl)-1,3-oxazol-2-yl]methyl}benzenesulfonamide

Produkt 1

HCID 58393121N-Cyclopropyl-4-methoxy-2,6-dimethyl-N-{[4-({4-[(2-methylpyridin-4-yl)methyl]piperazin-1-yl}carbonyl)-1,3-oxazol-2-yl]methyl}benzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of N-cyclopropyl-4-methoxy-2,6-dimethyl-N-{[4-(piperazin-1-ylcarbonyl)-1,3-oxazol-2-yl]methyl}benzenesulfonamide (30 mg, 0.07 mmol) in DCE (2 mL) were added 6-methyl-4-pyridinecarboxaldehyde (10 mg, 0.08 mmol) and AcOH (3 μL, 0.07 mmol) and the reaction mixture was stirred for 1 h at ambient temperature. STAB (20 mg, 0.09 mmol) was added and the reaction was stirred for 16 h. The reaction mixture was quenched with H2O (2 mL) and extracted with DCM (3×2 mL). The organic layer was dried over Na2SO4 and concentrated in vacuo. The resulting residue was purified using prep method D to afford the title compound.

Aufarbeitung

  1. additionSTAB (20 mg, 0.09 mmol) was added
  2. stirringthe reaction was stirred for 16 h
  3. customThe reaction mixture was quenched with H2O (2 mL)
  4. extractionextracted with DCM (3×2 mL)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified

Quellen und Nachweise

ORD-Eintrag
ord-b6b9c452cc3f4d4bb91caf83db590e06
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08623859B2

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