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 54569노트

반응식

HRID 54569 반응식
[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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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 ).

후처리

  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

출처 및 근거

ORD 기록
ord-7a2c6b62bcb34a1096833904cd486b42
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05622976

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