Trifluoroacetic acid → 3-bromo-6-(1-methyl-1H-pyrazol-4-yl)-4-(piperidin-3-ylmethoxy)pyrazolo[1,5-a]pyridine

HRID 1253546Notes

Reaction equation

HRID 1253546 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][N:5]2[CH:10]=[C:9]([C:11]3[CH:12]=[N:13][N:14]([CH3:16])[CH:15]=3)[CH:8]=[C:7]([O:17][CH2:18][CH:19]3[CH2:24][CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20]3)[C:6]=12.FC(F)(F)C(O)=O>ClCCl>[Br:1][C:2]1[CH:3]=[N:4][N:5]2[CH:10]=[C:9]([C:11]3[CH:12]=[N:13][N:14]([CH3:16])[CH:15]=3)[CH:8]=[C:7]([O:17][CH2:18][CH:19]3[CH2:24][CH2:23][CH2:22][NH:21][CH2:20]3)[C:6]=12

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58404902Tert-butyl 3-(((3-bromo-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-4-yl)oxy)methyl)piperidine-1-carboxylate

Product 1

HCID 584046703-bromo-6-(1-methyl-1H-pyrazol-4-yl)-4-(piperidin-3-ylmethoxy)pyrazolo[1,5-a]pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-butyl 3-({[3-bromo-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-4-yl]oxy}methyl)piperidine-1-carboxylate (55.0 mg, 0.112 mmol) was dissolved in dichloromethane (3 ml) at 0° C. Trifluoroacetic acid (1.0 ml) was added and the solution was allowed to stir for 30 minutes. The solution was concentrated to a colorless oil, which was dissolved in 2 ml of methanol and eluted through a bicarbonate resin cartridge (StratoSpheres SPE, PL-HCO3 MP SPE), flushing with 10 mL of methanol. The solution was concentrated and eluted through a second bicarbonate resin cartridge to afford 3-bromo-6-(1-methyl-1H-pyrazol-4-yl)-4-(piperidin-3-ylmethoxy)pyrazolo[1,5-a]pyridine. 1H NMR (500 MHz, DMSO-d6) δ 8.62 (s, 1H); 8.28 (s, 1H); 8.01 (s, 1H); 7.96 (s, 1H); 6.89 (s, 1H); 3.98-4.06 (m, 2H); 3.85 (s, 3H), 3.12-3.16 (m, 1H); 2.84-2.89 (m, 1H); 1.92-2.01 (m, 1H); 1.84-1.90 (m, 1H); 1.58-1.64 (m, 1H); 1.20-1.45 (m, 4H). LRMS (ESI) calculated for C17H2179BrN5O [M+H]+, 390.1; found 390.0.

Workup

  1. concentrationThe solution was concentrated to a colorless oil, which
  2. dissolutionwas dissolved in 2 ml of methanol
  3. washeluted through a bicarbonate resin cartridge (StratoSpheres SPE, PL-HCO3 MP SPE)
  4. customflushing with 10 mL of methanol
  5. concentrationThe solution was concentrated
  6. washeluted through a second bicarbonate resin cartridge

Sources & evidence

ORD record
ord-b199d42cd75e4d92a84cf5e839e88a9f
Source dataset
uspto-grants-2013_06
Patent number
US08455477B2

Reaction notes

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