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

HRID 54562ノート

反応式

HRID 54562 の反応式
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

参加物

9

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 887Methanol溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-ce154569607b4a6aae09e56b9c7bffc2
出典データセット
uspto-grants-1997_04
特許番号
US05622976

反応ノート

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