Potassium Hydroxide → 3-[[2-{1-(4-Fluorobenzyl)piperidin-4-yl}ethyl]carbamoyl]-5-(4-cyanophenyl)-1,2,4-oxadiazole fumarate

HRID 54562노트

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HRID 54562 반응식
Cl.N1CCC(CCNC(C2N=C(C3C=CC(C#N)=CC=3)ON=2)=O)CC1.FC1C=CC(C=O)=CC=1.[OH-].[K+].[BH4-].[Na+].[F:39][C:40]1[CH:70]=[CH:69][C:43]([CH2:44][N:45]2[CH2:50][CH2:49][CH:48]([CH2:51][CH2:52][NH:53][C:54]([C:56]3[N:60]=[C:59]([C:61]4[CH:66]=[CH:65][C:64]([C:67]#[N:68])=[CH:63][CH:62]=4)[O:58][N:57]=3)=[O:55])[CH2:47][CH2:46]2)=[CH:42][CH:41]=1.[C:71]([OH:78])(=[O:77])/[CH:72]=[CH:73]/[C:74]([OH:76])=[O:75]>CO.C(O)C>[C:71]([OH:78])(=[O:77])/[CH:72]=[CH:73]/[C:74]([OH:76])=[O:75].[F:39][C:40]1[CH:41]=[CH:42][C:43]([CH2:44][N:45]2[CH2:50][CH2:49][CH:48]([CH2:51][CH2:52][NH:53][C:54]([C:56]3[N:60]=[C:59]([C:61]4[CH:62]=[CH:63][C:64]([C:67]#[N:68])=[CH:65][CH:66]=4)[O:58][N:57]=3)=[O:55])[CH2:47][CH2:46]2)=[CH:69][CH:70]=1

참가 물질

9

반응물 6

HCID 14797Potassium HydroxideHCID 680234-FluorobenzaldehydeHCID 444972Fumaric AcidHCID 4311764Sodium borohydrideHCID 98457333-[[2-{1-(4-Fluorobenzyl)piperidin-4-yl}ethyl]carbamoyl]-5-(4-cyanophenyl)-1,2,4-oxadiazoleHCID 199592533-[{2-(Piperidin-4-yl)ethyl}carbamoyl]-5-(4-cyanophenyl)-1,2,4-oxadiazole hydrochloride

생성물 1

HCID 199592613-[[2-{1-(4-Fluorobenzyl)piperidin-4-yl}ethyl]carbamoyl]-5-(4-cyanophenyl)-1,2,4-oxadiazole fumarate

시약·촉매·용매 2

HCID 702Ethanol용매HCID 887Methanol용매2회

실험 절차

To a mixture of 3-[{2-(piperidin-4-yl)ethyl}carbamoyl]-5-(4-cyanophenyl)-1,2,4-oxadiazole hydrochloride (0.7 g), 4-fluorobenzaldehyde (0.24 g) and molecular sieves 4A (1.0 g) in methanol (7 ml) was added 1M solution of potassium hydroxide in methanol (1.93 ml). After stirring for 5 hours at ambient temperature, sodium borohydride (73 mg) was added to the mixture under ice cooling. The mixture was stirred for 20 minutes and evaporated in vacuo. The residue was dissolved in ethyl acetate and washed with water, brine, dried over magnesium sulfate and evaporated in vacuo to give a residue containing 3-[[2-{1-(4-fluorobenzyl)piperidin-4-yl}ethyl]carbamoyl]-5-(4-cyanophenyl)-1,2,4-oxadiazole. The residue and fumaric acid (0.11 g) were dissolved in hot ethanol (10 ml) and recrystallized to afford 3-[[2-{1-(4-fluorobenzyl)piperidin-4-yl}ethyl]carbamoyl]-5-(4-cyanophenyl)-1,2,4-oxadiazole fumarate (0.50 g).

후처리

  1. stirringThe mixture was stirred for 20 minutes
  2. customevaporated in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with water, brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customto give a residue
  8. customrecrystallized

출처 및 근거

ORD 기록
ord-ce154569607b4a6aae09e56b9c7bffc2
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05622976

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