Sodium Bicarbonate → [1-[2-[(Methylsulphonyl)amino]ethyl]-4-piperidinyl]methyl[2-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]carbamate

HRID 53246

Reaktionsgleichung

Reaktionsgleichung von HRID 53246
[CH3:1][C:2]1[N:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[NH:13][C:14](Cl)=O)[O:4][N:3]=1.OC[CH:19]1[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][NH:27][S:28]([CH3:31])(=[O:30])=[O:29])[CH2:21][CH2:20]1.[C:32](=[O:35])(O)[O-:33].[Na+]>C1(C)C=CC=CC=1.C(O)C>[CH3:31][S:28]([NH:27][CH2:26][CH2:25][N:22]1[CH2:21][CH2:20][CH:19]([O:33][C:32](=[O:35])[N:13]([CH3:14])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[C:5]2[O:4][N:3]=[C:2]([CH3:1])[N:6]=2)[CH2:24][CH2:23]1)(=[O:29])=[O:30]

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 19962114N-(2-(4-(hydroxymethyl)piperidin-1-yl)ethyl)methanesulfonamideHCID 19962135[2-(3-Methyl-1,2,4-oxadiazol-5-yl)phenyl]carbamoyl Chloride

Produkt 1

HCID 70079874[1-[2-[(Methylsulphonyl)amino]ethyl]-4-piperidinyl]methyl[2-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]carbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21863594Toluene ethanolLösungsmittel

Versuchsvorschrift

[2-(3-Methyl-1,2,4-oxadiazol-5-yl)phenyl]carbamoyl chloride (7.5 g) was placed in a flask equipped with an air stirrer and ground to a powder N-[2-[4-(Hydroxymethyl)-1-piperidinyl]ethyl]methanesulphonamide (9.33 g) was added and the solids intimately mixed under nitrogen for 10 min at room temperature. The mixture was stirred under a stream of nitrogen at 150° for 10 min. The mixture was allowed to cool then toluene/ethanol (10:1; 110 ml) was cautiously added followed by 8% sodium bicarbonate solution. The mixture was vigorously stirred, the layers were separated and the aqueous phase extracted with 10% ethanol in dichloromethane (4×100 ml). The organic solutions were combined and dried and concentrated in vacuo to give a beige solid. This was purified by FCC eluting with System A (100:8:1) to give the title compound (11.83 g) as fluffy off-white needles.

Aufarbeitung

  1. customequipped with an air stirrer
  2. additionthe solids intimately mixed under nitrogen for 10 min at room temperature
  3. temperatureto cool
  4. stirringThe mixture was vigorously stirred
  5. customthe layers were separated
  6. extractionthe aqueous phase extracted with 10% ethanol in dichloromethane (4×100 ml)
  7. customdried
  8. concentrationconcentrated in vacuo
  9. customto give a beige solid
  10. customThis was purified by FCC
  11. washeluting with System A (100:8:1)

Quellen und Nachweise

ORD-Eintrag
ord-6d73ce3c728e48c89310726c630ef4b7
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05618827

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