5-(((2-Aminoethyl)thio)methyl)-N,N-dimethyl-2-furanmethanamine → 3-{2-[(5-Dimethylaminomethyl-2-furyl)methylthio]ethylamino}-4-(3-pyridyl)methylamino-1,2,5-thiadiazole 1-oxide

HRID 2418120Notes

Reaction equation

HRID 2418120 reaction equation
CO[C:3]1[C:7]([NH:8][CH2:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[N:6][S:5](=[O:16])[N:4]=1.[CH3:17][N:18]([CH2:20][C:21]1[O:25][C:24]([CH2:26][S:27][CH2:28][CH2:29][NH2:30])=[CH:23][CH:22]=1)[CH3:19]>CO>[CH3:19][N:18]([CH2:20][C:21]1[O:25][C:24]([CH2:26][S:27][CH2:28][CH2:29][NH:30][C:3]2[C:7]([NH:8][CH2:9][C:10]3[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=3)=[N:6][S:5](=[O:16])[N:4]=2)=[CH:23][CH:22]=1)[CH3:17]

Participants

4

Reactant 2

HCID 1622035-(((2-Aminoethyl)thio)methyl)-N,N-dimethyl-2-furanmethanamineHCID 204020453-Methoxy-4-(3-pyridyl)methylamino-1,2,5-thiadiazole 1-oxide

Product 1

HCID 159641483-{2-[(5-Dimethylaminomethyl-2-furyl)methylthio]ethylamino}-4-(3-pyridyl)methylamino-1,2,5-thiadiazole 1-oxide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To the methanol solution of 3-methoxy-4-(3-pyridyl)methylamino-1,2,5-thiadiazole 1-oxide produced in Step A was added a solution of 2-[(5-dimethylaminomethyl-2-furyl)methylthio]ethylamine (4.0 g; 18.7 mmoles) in 30 ml of methanol. The reaction mixture was stirred at ambient temperatures for 18 hours and the solvent was removed in vacuo. The residue was placed on 500 g of silica gel (230-400 mesh) and purified by flash chromatography using a gradient elution of acetonitrile-methanol. After combining the appropriate fractions, the title compound was obtained as an amber oil (4.25 g) containing one mole of methanol.

Workup

  1. customthe solvent was removed in vacuo
  2. custompurified by flash chromatography
  3. washa gradient elution of acetonitrile-methanol

Sources & evidence

ORD record
ord-d8a12b780c30441490d3e97e6e18b140
Source dataset
uspto-grants-1984_09
Patent number
US04471122

Reaction notes

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