Pyridine → 4-(5-Furo[3,2-c]pyridin-2-yl-[1,2,4]oxadiazol-3-ylmethyl)piperidine-1-carboxylic acid propyl ester

HRID 217195

반응식

HRID 217195 반응식
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][C:8]2[N:12]=[C:11]([C:13]3[O:21][C:20]4[CH:19]=[CH:18][N:17]=[CH:16][C:15]=4[CH:14]=3)[O:10][N:9]=2)[CH2:3][CH2:2]1.N1C=CC=CC=1.[CH2:28]([O:31][C:32](Cl)=[O:33])[CH2:29][CH3:30]>C(Cl)Cl.CCOCC>[CH2:28]([O:31][C:32]([N:1]1[CH2:6][CH2:5][CH:4]([CH2:7][C:8]2[N:12]=[C:11]([C:13]3[O:21][C:20]4[CH:19]=[CH:18][N:17]=[CH:16][C:15]=4[CH:14]=3)[O:10][N:9]=2)[CH2:3][CH2:2]1)=[O:33])[CH2:29][CH3:30]

참가 물질

6

반응물 3

HCID 1049PyridineHCID 7998Propyl chloroformateHCID 116305842-(3-Piperidin-4-ylmethyl-[1,2,4]oxadiazol-5-yl)furo[3,2-c]pyridine

생성물 1

HCID 576594274-(5-Furo[3,2-c]pyridin-2-yl-[1,2,4]oxadiazol-3-ylmethyl)piperidine-1-carboxylic acid propyl ester

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매2회

실험 절차

A solution of 2-(3-piperidin-4-ylmethyl-[1,2,4]oxadiazol-5-yl)furo[3,2-c]pyridine (Preparation 12, 0.65 g, 2.3 mmol) and pyridine (0.37 mL, 4.6 mmol) in anhydrous CH2Cl2 (25 mL) was added via cannula to a stirred solution of n-PrOCOCl (0.51 mL, 4.6 mmol) in anhydrous CH2Cl2 (35 mL). After 16 h, the reaction mixture was diluted with Et2O (200 mL), before being washed with H2O (100 mL), saturated aqueous Na2CO3 (100 mL), and H2O (100 mL). The organic phase was dried, filtered and concentrated. Flash chromatographic purification (EtOAc) of the residue furnished the title compound: RT=3.11 min; m/z (ES+)=371.1 [M+H]+.

후처리

  1. washbefore being washed with H2O (100 mL), saturated aqueous Na2CO3 (100 mL), and H2O (100 mL)
  2. customThe organic phase was dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customFlash chromatographic purification (EtOAc) of the residue

출처 및 근거

ORD 기록
ord-22fbb2b11e844395951e03b943608dc0
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193359B2

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