Diisopropylethylamine → 4-Methoxy-2,6-dimethyl-N-{5-[4-(1-methyl-piperidin-4-ylmethyl)-piperazine-1-carbonyl]-1,3,4-oxadiazol-2-ylmethyl}-benzenesulfonamide

HRID 469114

Reaktionsgleichung

Reaktionsgleichung von HRID 469114
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([S:10](Cl)(=[O:12])=[O:11])=[C:5]([CH3:14])[CH:4]=1.Cl.Cl.Cl.[NH2:18][CH2:19][C:20]1[O:24][C:23]([C:25]([N:27]2[CH2:32][CH2:31][N:30]([CH2:33][CH:34]3[CH2:39][CH2:38][N:37]([CH3:40])[CH2:36][CH2:35]3)[CH2:29][CH2:28]2)=[O:26])=[N:22][N:21]=1.CCN(C(C)C)C(C)C>C(Cl)Cl.C([O-])(O)=O.[Na+]>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([S:10]([NH:18][CH2:19][C:20]2[O:24][C:23]([C:25]([N:27]3[CH2:32][CH2:31][N:30]([CH2:33][CH:34]4[CH2:39][CH2:38][N:37]([CH3:40])[CH2:36][CH2:35]4)[CH2:29][CH2:28]3)=[O:26])=[N:22][N:21]=2)(=[O:12])=[O:11])=[C:5]([CH3:14])[CH:4]=1

Komponenten

6

Edukt 3

HCID 81531DiisopropylethylamineHCID 159174964-Methoxy-2,6-dimethylbenzene-1-sulfonyl chlorideHCID 67217756(5-Aminomethyl-1,3,4-oxadiazol-2-yl)-[4-(1-methyl-piperidin-4-ylmethyl)-piperazin-1-yl]-methanone trihydrochloride

Produkt 1

HCID 461764114-Methoxy-2,6-dimethyl-N-{5-[4-(1-methyl-piperidin-4-ylmethyl)-piperazine-1-carbonyl]-1,3,4-oxadiazol-2-ylmethyl}-benzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
-30 °C

Versuchsvorschrift

4-methoxy-2,6-dimethylbenzenesulfonyl chloride (118 mg, 0.5 mmol) was added to a suspension of (5-Amino methyl-1,3,4-oxadiazol-2-yl)-[4-(1-methyl-piperidin-4-ylmethyl)-piperazin-1-yl]-methanone trihydrochloride (200 mg, 0.43 mmol) in DCM, under N2 and the mixture was cooled to −30° C. DIPEA (376 μL, 2.15 mmol) was added over about 3 min and the resultant pink solution was stirred at −30° C. for 30 min and then at ambient temperature for 16 h. The mixture was diluted with saturated aqueous NaHCO3 and extracted with DCM (×2). The combined organic extracts were dried over MgSO4 and concentrated in vacuo to a brown gum which was purified using FCC, eluting with 5% NH3 (2.0 M in MeOH) in DCM, to give the title compound as a clear gum.

Aufarbeitung

  1. waitat ambient temperature for 16 h
  2. extractionextracted with DCM (×2)
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. concentrationconcentrated in vacuo to a brown gum which
  5. customwas purified
  6. washeluting with 5% NH3 (2.0 M in MeOH) in DCM

Quellen und Nachweise

ORD-Eintrag
ord-a479d09a35a64ab68e34c28ba197e7a4
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08623859B2

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