2,4,6-trifluoro-N-methyl-N-[6-(1-t-butoxycarbonyl-piperidin-4-ylcarbonyl)-pyridin-2-yl]-benzamide → 2,4,6-trifluoro-N-methyl-N-[6-(piperidin-4-ylcarbonyl)-pyridin-2-yl]-benzamide
Reaction equation
[F:1][C:2]1[CH:32]=[C:31]([F:33])[CH:30]=[C:29]([F:34])[C:3]=1[C:4]([N:6]([CH3:28])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([CH:15]2[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][CH2:16]2)=[O:14])[N:8]=1)=[O:5]>FC(F)(F)C(O)=O.C(Cl)Cl>[F:34][C:29]1[CH:30]=[C:31]([F:33])[CH:32]=[C:2]([F:1])[C:3]=1[C:4]([N:6]([CH3:28])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([CH:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)=[O:14])[N:8]=1)=[O:5]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
Dissolve the 2,4,6-trifluoro-N-methyl-N-[6-(1-t-butoxycarbonyl-piperidin-4-ylcarbonyl)-pyridin-2-yl]-benzamide in 50% trifluoroacetic acid/CH2Cl2 (24 mL) and stir for 45 min. Remove volatiles under reduced pressure and extract with ethyl acetate and aqueous NaOH (2M). Combine the organic layers and dry with sodium sulfate. Concentrate and purify the residue by chromatography (silica gel/6% of (2M NH3 in methanol)/CH2Cl2) to afford 2,4,6-trifluoro-N-methyl-N-[6-(piperidin-4-ylcarbonyl)-pyridin-2-yl]-benzamide (77 mg, 85% yield).
Workup
- extractionRemove volatiles under reduced pressure and extract with ethyl acetate and aqueous NaOH (2M)
- dry with materialCombine the organic layers and dry with sodium sulfate
- concentrationConcentrate
- custompurify the residue by chromatography (silica gel/6% of (2M NH3 in methanol)/CH2Cl2)
Sources & evidence
- ORD record
- ord-700ea2e2d4394b46bbfbbe304e5e241a
- Source dataset
- uspto-grants-2008_09
- Patent number
- US07423050B2
Reaction notes
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