Sodium Bicarbonate → 3-Ethyl-5-[1-(2-fluoro-4-[(5-nitro-2-furyl)methyl]aminophenyl)-4-piperidyl]-2,3-di hydro-1,3,4-oxadiazol-2-one

HRID 515436노트

반응식

HRID 515436 반응식
[CH2:1]([N:3]1[N:7]=[C:6]([CH:8]2[CH2:13][CH2:12][N:11]([C:14]3[CH:19]=[CH:18][C:17](/[N:20]=[CH:21]/[C:22]4[O:23][C:24]([N+:27]([O-:29])=[O:28])=[CH:25][CH:26]=4)=[CH:16][C:15]=3[F:30])[CH2:10][CH2:9]2)[O:5][C:4]1=[O:31])[CH3:2].C([BH3-])#N.[Na+].C(=O)(O)[O-].[Na+]>CC(O)=O.CO>[CH2:1]([N:3]1[N:7]=[C:6]([CH:8]2[CH2:9][CH2:10][N:11]([C:14]3[CH:19]=[CH:18][C:17]([NH:20][CH2:21][C:22]4[O:23][C:24]([N+:27]([O-:29])=[O:28])=[CH:25][CH:26]=4)=[CH:16][C:15]=3[F:30])[CH2:12][CH2:13]2)[O:5][C:4]1=[O:31])[CH3:2]

참가 물질

6

반응물 3

HCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 178463008HCID 178463008, 화합물

생성물 1

HCID 716170433-Ethyl-5-[1-(2-fluoro-4-[(5-nitro-2-furyl)methyl]aminophenyl)-4-piperidyl]-2,3-di hydro-1,3,4-oxadiazol-2-one수율 83%

시약·촉매·용매 2

HCID 176Acetic Acid촉매HCID 887Methanol용매

실험 절차

3-Ethyl-5-[1-(2-fluoro-4-[(E)-1-(5-nitro-2-furyl)methylidene]aminophenyl)-4-piperidyl]-2,3-dihydro-1,3,4-oxadiazol-2-one (9 g, 0.43 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-ethyl-5-[1-(2-fluoro-4-[(5-nitro-2-furyl)methyl]aminophenyl)-4-piperidyl]-2,3-dihydro-1,3,4-oxadi azol-2-one (10g, 357 mg, 83%).

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-16287b7a877f475b9a495640abf428d3
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09108960B2

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