Sodium Hydroxide → 2-(4-propylphenyl)-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide

HRID 361429Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 361429
[OH-].[Na+].C(OC([N:10]([C:29]1[C:34]([O:35][CH3:36])=[N:33][C:32]([CH3:37])=[CH:31][N:30]=1)[S:11]([C:14]1[C:15]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][CH3:28])=[CH:22][CH:21]=2)=[N:16][CH:17]=[CH:18][CH:19]=1)(=[O:13])=[O:12])=O)C(C)C>CO>[CH2:26]([C:23]1[CH:24]=[CH:25][C:20]([C:15]2[C:14]([S:11]([NH:10][C:29]3[C:34]([O:35][CH3:36])=[N:33][C:32]([CH3:37])=[CH:31][N:30]=3)(=[O:12])=[O:13])=[CH:19][CH:18]=[CH:17][N:16]=2)=[CH:21][CH:22]=1)[CH2:27][CH3:28]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 21186267N-(isobutoxycarbonyl)-2-(4-propylphenyl)-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide

Produkt 1

HCID 211862622-(4-propylphenyl)-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamideAusbeute 71,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

2M Sodium hydroxide solution (1 ml) was added to a solution of N-(isobutoxycarbonyl)-2-(4-propylphenyl)-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide (0.7 g) in methanol (2 ml) and the reaction mixture stirred for 17 hours at ambient temperature. The methanol was removed by evaporation and water (20 ml) was added. The reaction mixture was extracted with ethyl acetate (4×15 ml), the combined organic extracts were dried (MgSO4) and then the solvent was removed by evaporation. The resultant oil was purified by eluting with 30% ethyl acetate/isohexane through a silica gel Mega Bond Elut column, followed by trituration with isohexane/diethyl ether to give 2-(4-propylphenyl)-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide (0.4 g) as a solid, m.p. 70°-72° C.; mass spectrum (+ve ESP): 399 (M+H)+.

Aufarbeitung

  1. customThe methanol was removed by evaporation and water (20 ml)
  2. additionwas added
  3. extractionThe reaction mixture was extracted with ethyl acetate (4×15 ml)
  4. dry with materialthe combined organic extracts were dried (MgSO4)
  5. customthe solvent was removed by evaporation
  6. customThe resultant oil was purified
  7. washby eluting with 30% ethyl acetate/isohexane through a silica gel Mega Bond Elut column

Quellen und Nachweise

ORD-Eintrag
ord-9afaa90f400e46278a184fb887194562
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05866568

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