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

HRID 217195

Reaction equation

HRID 217195 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-22fbb2b11e844395951e03b943608dc0
Source dataset
uspto-grants-2012_06
Patent number
US08193359B2

Linked notes

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