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

HRID 404237Notes

Reaction equation

HRID 404237 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

HCID 674431142,4,6-trifluoro-N-methyl-N-[6-(1-t-butoxycarbonyl-piperidin-4-ylcarbonyl)-pyridin-2-yl]-benzamide

Product 1

HCID 179803162,4,6-trifluoro-N-methyl-N-[6-(piperidin-4-ylcarbonyl)-pyridin-2-yl]-benzamideYield 85%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

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

  1. extractionRemove volatiles under reduced pressure and extract with ethyl acetate and aqueous NaOH (2M)
  2. dry with materialCombine the organic layers and dry with sodium sulfate
  3. concentrationConcentrate
  4. custompurify the residue by chromatography (silica gel/6% of (2M NH3 in methanol)/CH2Cl2)

Sources & evidence

ORD record
ord-d5a76044d836465e914ee8a283474d00
Source dataset
uspto-grants-2014_06
Patent number
US08748459B2

Reaction notes

Loading…