Reaktion #473324

ord-028dfb019ee4490d9fcb863bbe8ba9f0

Reaktionsgleichung

C#Cc1cc(C(N)=O)c(Nc2cccc(CN3CCOCC3)n2)s1
5-Ethynyl-2-{[6-(morpholin-4-ylmethyl)pyridin-2-yl]amino}thiophene-3-carboxamide
CC(C)(C)C(=O)OCN=[N+]=[N-]
azidomethyl pivalate
O=C1O[C@H]([C@@H](O)CO)C([O-])=C1O.[Na+]
sodium ascorbate
→
CC(C)(C)C(=O)OCn1cc(-c2cc(C(N)=O)c(Nc3cccc(CN4CCOCC4)n3)s2)nn1
title compound
CC(C)(C)C(=O)OCn1cc(-c2cc(C(N)=O)c(Nc3cccc(CN4CCOCC4)n3)s2)nn1
[4-(4-(Aminocarbonyl)-5-{[6-(morpholin-4-ylmethyl)pyridin-2-yl]amino}-2-thienyl)-1H-1,2,3-triazol-1-yl]methyl pivalate

Edukte

C#Cc1cc(C(N)=O)c(Nc2cccc(CN3CCOCC3)n2)s1
5-Ethynyl-2-{[6-(morpholin-4-ylmethyl)pyridin-2-yl]amino}thiophene-3-carboxamide
CC(C)(C)C(=O)OCN=[N+]=[N-]
azidomethyl pivalate
—
CuSO4.5H2O
O=C1O[C@H]([C@@H](O)CO)C([O-])=C1O.[Na+]
sodium ascorbate

Reagenzien

Keine

Lösungsmittel

O
water
O
water
CN(C)C=O
DMF

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    EinengenThe reaction was concentrated to dryness
  2. 2
    Sonstigeevaporated
  3. 3
    TrocknenFlash chromatography (dry load, 0-10% MeOH/EtOAc)

Vorschrift

5-Ethynyl-2-{[6-(morpholin-4-ylmethyl)pyridin-2-yl]amino}thiophene-3-carboxamide (86 mg, 0.25 mmol) and azidomethyl pivalate (59 mg, 0.38 mmol) were combined in DMF (1.0 mL). CuSO4.5H2O (6.3 mg, 0.025 mmol) in water (0.2 mL) and sodium ascorbate (20 mg, 0.10 mmol) in water (0.2 mL) were added, and the reaction mixture was stirred at room temperature overnight. The reaction was concentrated to dryness, combined with MeOH and silica gel, and evaporated. Flash chromatography (dry load, 0-10% MeOH/EtOAc) afforded the title compound as a yellow solid.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08367706B2uspto-grants-2013_02