3-(Oxiran-2-yl)pyridine → HCID 20073151, compound

HRID 2292069Notes

Reaction equation

HRID 2292069 reaction equation
[O:1]1[CH2:3][CH:2]1[C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1.[NH2:10][CH:11]([CH3:22])[CH2:12][CH2:13][C:14]1[S:18][C:17]([C:19]([NH2:21])=[O:20])=[CH:16][CH:15]=1>CS(C)=O.O>[OH:1][CH:2]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1)[CH2:3][NH:10][CH:11]([CH3:22])[CH2:12][CH2:13][C:14]1[S:18][C:17]([C:19]([NH2:21])=[O:20])=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 133195613-(Oxiran-2-yl)pyridineHCID 198091485-(3-Aminobutyl)thiophene-2-carboxamide

Product 1

HCID 20073151HCID 20073151, compoundYield 9.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

606 mg of 3-[(RS)-2-oxiranyl]pyridine and 991 mg of (RS)-5-(3-aminobutyl)-2-thiophenecarboxamide were heated to 100° for 25 hours in 5 ml of DMSO. The reaction mixture was diluted with water and extracted three times with methylene chloride. The methylene chloride solutions were washed with water, dried and evaporated in a vacuum. Chromatography of the residue on silica gel with ether/methanol gave 149 mg of 5-[(RS)-3-[[(RS)-2-hydroxy-2-(3-pyridyl)ethyl]amino]butyl]-2-thiophenecarboxamide, ε201 =14420; ε268 =11310.

Workup

  1. extractionextracted three times with methylene chloride
  2. washThe methylene chloride solutions were washed with water
  3. customdried
  4. customevaporated in a vacuum

Sources & evidence

ORD record
ord-4ae8e8aa4e7e4db7a01f154439c0cda0
Source dataset
uspto-grants-1989_01
Patent number
US04800206

Reaction notes

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