3-Methyl-2-thiophenecarboxaldehyde → (3-Methylthien-2-ylmethyl)-[4-(5-methylthio-3-pyridin-4-yl-1H-1,2,4-triazol-1-yl)phenyl]amine

HRID 1280544Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1280544
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([S:13][CH3:14])=[N:11][C:10]([C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)=[N:9]2)=[CH:4][CH:3]=1.[CH3:21][C:22]1[CH:26]=[CH:25][S:24][C:23]=1[CH:27]=O.C([BH3-])#N.[Na+]>C(O)(=O)C.CO>[CH3:21][C:22]1[CH:26]=[CH:25][S:24][C:23]=1[CH2:27][NH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([S:13][CH3:14])=[N:11][C:10]([C:15]3[CH:16]=[CH:17][N:18]=[CH:19][CH:20]=3)=[N:9]2)=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 799113-Methyl-2-thiophenecarboxaldehydeHCID 5003444Sodium cyanoborohydrideHCID 184258711-(4-aminophenyl)-5-methylthio-3-(4-pyridyl)-1H-1,2,4-triazole

Produkt 1

HCID 18425879(3-Methylthien-2-ylmethyl)-[4-(5-methylthio-3-pyridin-4-yl-1H-1,2,4-triazol-1-yl)phenyl]amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 887MethanolLösungsmittel

Versuchsvorschrift

A stirred solution of 1-(4-aminophenyl)-5-methylthio-3-(4-pyridyl)-1H-1,2,4-triazole (Example 1) (100 mg, 0.35 mmol) and 3-methylthiophene-2-carboxaldehyde (44 mg, 0.35 mmol) in 5% acetic acid in MeOH (4 mL) at room temperature was treated with sodium cyanoborohydride (55 mg, 0.88 mmol) and the reaction mixture was further stirred at room temperature for 48 h. The reaction mixture was concentrated, diluted with EtOAc, washed with NaHCO3 solution, brine and dried (MgSO4). The residue obtained on concentration was flash chromatographed on silica gel and eluted with a gradient of dichloromethane/acetone (9/1 to 3/1). The title compound was obtained as a white solid (85 mg).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with EtOAc
  3. washwashed with NaHCO3 solution, brine
  4. dry with materialdried (MgSO4)
  5. customThe residue obtained on concentration
  6. customchromatographed on silica gel
  7. washeluted with a gradient of dichloromethane/acetone (9/1 to 3/1)

Quellen und Nachweise

ORD-Eintrag
ord-34d645a9fa704ad29676d2a9f47237ce
Quelldatensatz
uspto-grants-2002_09
Patentnummer
US06451820B1

Notizen zur Reaktion

Wird geladen…