1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-[(E)-2-[{2-(1-benzylpiperidin-4-yl)ethyl}carbamoyl]vinyl]-5-(4-cyanophenyl)-1,2,4-oxadiazole fumarate

HRID 54569Notes

Reaction equation

HRID 54569 reaction equation
[C:1](/[CH:4]=[CH:5]/[C:6]1[N:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=2)[O:8][N:7]=1)([OH:3])=[O:2].[CH2:19]([N:26]1[CH2:31][CH2:30][CH:29]([CH2:32][CH2:33][NH2:34])[CH2:28][CH2:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[OH2:35].[OH:36]N1C2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C>CN(C)C=O.O>[C:1]([OH:3])(=[O:2])/[CH:4]=[CH:5]/[C:6]([OH:36])=[O:35].[CH2:19]([N:26]1[CH2:31][CH2:30][CH:29]([CH2:32][CH2:33][NH:34][C:1](/[CH:4]=[CH:5]/[C:6]2[N:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=3)[O:8][N:7]=2)=[O:3])[CH2:28][CH2:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 18670022-(1-Benzylpiperidin-4-yl)ethan-1-amineHCID 27960291-Hydroxybenzotriazole hydrateHCID 199592323-{(E)-2-carboxyvinyl}-5-(4-cyanophenyl)-1,2,4-oxadiazole

Product 1

HCID 199593293-[(E)-2-[{2-(1-benzylpiperidin-4-yl)ethyl}carbamoyl]vinyl]-5-(4-cyanophenyl)-1,2,4-oxadiazole fumarateYield 110.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 3-{(E)-2-carboxyvinyl}-5-(4-cyanophenyl)-1,2,4-oxadiazole (0.25 g), 2-(1-benzylpiperidin-4-yl)ethylamine (0.23 g) and 1-hydroxybenzotriazole hydrate (0.16 g) in N,N-dimethylformamide (5 ml) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (0.20 ml) at 5° C. After stirring for 1 hour at ambient temperature, the mixture was poured into water and extracted with ethyl acetate. The extract was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica eluting with 2% methanol in chloroform and the fractions containing the object compound were evaporated in vacuo. The residue was dissolved in a solution of fumaric acid (71 mg) in ethanol to give 3-[(E)-2-[{2-(1-benzylpiperidin-4-yl)ethyl}carbamoyl]vinyl]-5-(4-cyanophenyl)-1,2,4-oxadiazole fumarate (0.32 g ).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was chromatographed on silica eluting with 2% methanol in chloroform
  6. additionthe fractions containing the object compound
  7. customwere evaporated in vacuo
  8. dissolutionThe residue was dissolved in a solution of fumaric acid (71 mg) in ethanol

Sources & evidence

ORD record
ord-7a2c6b62bcb34a1096833904cd486b42
Source dataset
uspto-grants-1997_04
Patent number
US05622976

Reaction notes

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