HCID 57659516, compound → HCID 136189049, compound

HRID 217200Notes

Reaction equation

HRID 217200 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]2[N:19]=[C:18]([C:20]3[O:28][C:27]4[CH:26]=[CH:25][N:24]=[CH:23][C:22]=4[C:21]=3[O:29]CC3C=CC=CC=3)[O:17][N:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CCO.C(Cl)Cl.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([CH2:14][C:15]2[N:19]=[C:18]([C:20]3[O:28][C:27]4[CH:26]=[CH:25][N:24]=[CH:23][C:22]=4[C:21]=3[OH:29])[O:17][N:16]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 1

HCID 57659516HCID 57659516, compound

Product 1

HCID 136189049HCID 136189049, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 4-[5-(3-benzyloxyfuro[3,2-c]pyridin-2-yl)-[1,2,4]oxadiazol-3-ylmethyl]-piperidine-1-carboxylic acid tert-butyl ester (Example 120, 200 mg, 500 μmol) and Pd (10% on C, 10 mg) in EtOH (10 mL) was stirred under a H2 atmosphere for 2.5 h. The mixture was diluted with CH2Cl2, to solubilise the product, before being filtered through celite. The filtrate was concentrated to furnish the title compound: RT=2.87 min; m/z (ES+)=401.1 [M+H]+.

Workup

  1. filtrationbefore being filtered through celite
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-f1862b3edfe844b3b31135755e1a0dde
Source dataset
uspto-grants-2012_06
Patent number
US08193359B2

Reaction notes

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