Sodium Bicarbonate → 3-Methyl-5-[1-(4-[(5-nitro-2-furyl)methyl]aminophenyl)-4-piperidyl]-2,3-dihydro-1,3,4-oxadiazol-2-one

HRID 515431노트

반응식

HRID 515431 반응식
[CH3:1][N:2]1[N:6]=[C:5]([CH:7]2[CH2:12][CH2:11][N:10]([C:13]3[CH:18]=[CH:17][C:16](/[N:19]=[CH:20]/[C:21]4[O:22][C:23]([N+:26]([O-:28])=[O:27])=[CH:24][CH:25]=4)=[CH:15][CH:14]=3)[CH2:9][CH2:8]2)[O:4][C:3]1=[O:29].C([BH3-])#N.[Na+].C(=O)(O)[O-].[Na+]>CC(O)=O.CO>[CH3:1][N:2]1[N:6]=[C:5]([CH:7]2[CH2:8][CH2:9][N:10]([C:13]3[CH:14]=[CH:15][C:16]([NH:19][CH2:20][C:21]4[O:22][C:23]([N+:26]([O-:28])=[O:27])=[CH:24][CH:25]=4)=[CH:17][CH:18]=3)[CH2:11][CH2:12]2)[O:4][C:3]1=[O:29]

참가 물질

6

반응물 3

HCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 178481743HCID 178481743, 화합물

생성물 1

HCID 716170383-Methyl-5-[1-(4-[(5-nitro-2-furyl)methyl]aminophenyl)-4-piperidyl]-2,3-dihydro-1,3,4-oxadiazol-2-one수율 86%

시약·촉매·용매 2

HCID 176Acetic Acid촉매HCID 887Methanol용매

실험 절차

3-Methyl-5-[1-(4-[(E)-1-(5-nitro-2-furyl)methylidene]aminophenyl)-4-piperidyl]-2,3-dihydro-1,3,4-oxadiazol-2-one (9b, 0.40 g, 1 mmol) on reduction with sodiumcyanoborohydride (0.12 g, 2 mmol) in the presence of catalytic amount of CH3COOH (3 drops) in methanol at 0° C. for 12 h. After completion of the reaction as indicated by TLC, the reaction mixture is neutralized with sodium bi carbonate and extracted into chloroform. The crude product thus obtained was purified by column chromatography using ethyl acetate-hexane (8:2) as eluant to obtain product 3-methyl-5-[1-(4-[(5-nitro-2-furyl)methyl]aminophenyl)-4-piperidyl]-2,3-dihydro-1,3,4-oxadiazol-2-one (10b, 343 mg, 86%).

후처리

  1. customAfter completion of the reaction
  2. extractionextracted into chloroform
  3. customThe crude product thus obtained
  4. customwas purified by column chromatography

출처 및 근거

ORD 기록
ord-cef4322ad6c94228bd62808f1211d5fd
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09108960B2

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