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 1280544Notes

Reaction equation

HRID 1280544 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-34d645a9fa704ad29676d2a9f47237ce
Source dataset
uspto-grants-2002_09
Patent number
US06451820B1

Reaction notes

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