Water → 3-Pyridinecarboxylic acid, 6-(4-amino-1-piperidinyl)-, ethyl ester
Reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]([N:12]2[CH2:17][CH2:16][CH:15](C(=O)N)[CH2:14][CH2:13]2)=[N:10][CH:11]=1)=[O:5])[CH3:2].FC(F)(F)C(OC1C(OC(=O)C(F)(F)F)=C(I)C=CC=1)=O.O.C(#[N:45])C>>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]([N:12]2[CH2:17][CH2:16][CH:15]([NH2:45])[CH2:14][CH2:13]2)=[N:10][CH:11]=1)=[O:5])[CH3:2]Participants
Conditions
- Temperature
- 65 °C
Procedure
A solution comprising 4-carbamoyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-5′-carboxylic acid ethyl ester (step a) (2.04 g, 7.36-mmol) and bis(trifluoroacetoxy) iodobenzene (3.80 g, 8.83 mmol) in acetonitrile (13 ml) is treated with water (5 ml) and heated to 65° C. for 30 hours. The solvent is partially removed in vacuo and the resulting solution is acidified to pH1 using 12 M HCl. The solution is extracted with ethyl acetate and this organic portion is discarded. The aqueous portion is basified to pH 8-9 using 2M potassium carbonate solution and then extracted with ethyl acetate and dichloromethane. The organic portions are washed with brine, dried (Na2SO4) and concentrated in vacuo. The resulting residue is triturated with diethyl ether followed by diethyl ether/ethyl acetate (1:1, 5×0.7 ml) and dried in vacuo to yield the title compound as an off-white solid. MS (ES+) m/e 250 (MH+)
Workup
- customThe solvent is partially removed in vacuo
- extractionThe solution is extracted with ethyl acetate
- extractionextracted with ethyl acetate and dichloromethane
- washThe organic portions are washed with brine
- dry with materialdried (Na2SO4)
- concentrationconcentrated in vacuo
- customThe resulting residue is triturated with diethyl ether
- customdried in vacuo
Sources & evidence
- ORD record
- ord-6b49754971084639a9b9cc7d6206c91f
- Source dataset
- uspto-grants-2012_02
- Patent number
- US08114877B2
Reaction notes
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