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

HRID 217195

反応式

HRID 217195 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-22fbb2b11e844395951e03b943608dc0
出典データセット
uspto-grants-2012_06
特許番号
US08193359B2

関連ノート

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