Trifluoroacetic acid → HCID 178420066, compound

HRID 1441287Notes

Reaction equation

HRID 1441287 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:11]=[C:10]([CH:12]2[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13]2)[NH:9][N:8]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[NH:15]1[CH2:14][CH2:13][CH:12]([C:10]2[CH:11]=[C:7]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)[NH:8][N:9]=2)[CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86624608HCID 86624608, compound

Product 1

HCID 178420066HCID 178420066, compoundYield 108.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 4-(3-pyridin-2-yl-1H-pyrazol-5-yl)piperidine-1-carboxylate (1.46 g, 4.45 mmol) was dissolved in 15 ml DCM. Trifluoroacetic acid (5 ml) was added gradually and the resulting solution was stirred at ambient temperature for 3 h and was then concentrated in vacuo. The residue was dissolved in 4:1 MeOH/water and treated with MP-carbonate resin (5 g, 2.55 mmol/g). After stirring overnight the reaction was filtered and the filtrate was concentrated in vacuo to provide 1.1 g of 2-(3-piperidin-4-yl-1H-pyrazol-5-yl)pyridine (1-4) as a tan solid. δ 8.56 (d, J=3.9 Hz, 1H), 7.84 (m, 2H), 7.21 (m, 1H), 6.65 (s, 1H), 3.22 (m, 3H), 2.87 (m, 2H), 2.03 (d, J=12.8 Hz, 2H), 1.71 (d, J=10.3 Hz, 2H). m/z (m+1): 229.3,

Workup

  1. concentrationwas then concentrated in vacuo
  2. dissolutionThe residue was dissolved in 4:1 MeOH/water
  3. additiontreated with MP-carbonate resin (5 g, 2.55 mmol/g)
  4. stirringAfter stirring overnight the reaction
  5. filtrationwas filtered
  6. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-5c544314321c40138ab7ca4382221bab
Source dataset
uspto-grants-2010_02
Patent number
US07655649B2

Reaction notes

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