Hydrochloric Acid → 2-{[6-(Morpholin-4-ylmethyl)pyridin-2-yl]amino}-5-(1H-1,2,3-triazol-4-yl)thiophene-3-carboxamide

HRID 386143Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 386143
C(OC[N:9]1[CH:13]=[C:12]([C:14]2[S:15][C:16]([NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][N:30]4[CH2:35][CH2:34][O:33][CH2:32][CH2:31]4)[N:24]=3)=[C:17]([C:19]([NH2:21])=[O:20])[CH:18]=2)[N:11]=[N:10]1)(=O)C(C)(C)C.[OH-].[Na+].Cl>CO.O>[N:30]1([CH2:29][C:25]2[N:24]=[C:23]([NH:22][C:16]3[S:15][C:14]([C:12]4[N:11]=[N:10][NH:9][CH:13]=4)=[CH:18][C:17]=3[C:19]([NH2:21])=[O:20])[CH:28]=[CH:27][CH:26]=2)[CH2:31][CH2:32][O:33][CH2:34][CH2:35]1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59525795[4-(4-(Aminocarbonyl)-5-{[6-(morpholin-4-ylmethyl)pyridin-2-yl]amino}-2-thienyl)-1H-1,2,3-triazol-1-yl]methyl pivalate

Produkt 1

HCID 1785135682-{[6-(Morpholin-4-ylmethyl)pyridin-2-yl]amino}-5-(1H-1,2,3-triazol-4-yl)thiophene-3-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel2×

Versuchsvorschrift

To a suspension of [4-(4-(aminocarbonyl)-5-{[6-(morpholin-4-ylmethyl)pyridin-2-yl]amino}-2-thienyl)-1H-1,2,3-triazol-1-yl]methyl pivalate (70 mg, 0.14 mmol) in MeOH (1.5 mL) and water (1.0 mL) was added NaOH (1.0 M, 0.310 ml, 0.31 mmol). The mixture was stirred at room temperature for 45 min (the suspension became a clear orange solution). The reaction was neutralized with 2 N HCl (0.150 ml), diluted with water, and extracted with 5:1 CH2Cl2:MeOH (3×). The combined organic extracts were dried (MgSO4), filtered, combined with silica gel, and evaporated to dryness. Flash chromatography (dry load, 0-10% MeOH/CH2Cl2) yielded the title compound as a colorless solid.

Aufarbeitung

  1. extractionextracted with 5:1 CH2Cl2
  2. dry with materialThe combined organic extracts were dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated to dryness
  5. dry with materialFlash chromatography (dry load, 0-10% MeOH/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-55ff82842eea4085b29e2ebea4fcaad4
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367706B2

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