Trifluoroacetic acid → 3-(2,7-diazaspiro[3.5]non-2-ylmethyl)-4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine

HRID 1253528Notes

Reaction equation

HRID 1253528 reaction equation
[CH3:1][O:2][C:3]1[C:4]2[N:5]([N:15]=[CH:16][C:17]=2[CH2:18][N:19]2[CH2:22][C:21]3([CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]3)[CH2:20]2)[CH:6]=[C:7]([C:9]2[CH:10]=[N:11][N:12]([CH3:14])[CH:13]=2)[CH:8]=1.FC(F)(F)C(O)=O>ClCCl>[CH2:20]1[C:21]2([CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[CH2:22][N:19]1[CH2:18][C:17]1[CH:16]=[N:15][N:5]2[CH:6]=[C:7]([C:9]3[CH:10]=[N:11][N:12]([CH3:14])[CH:13]=3)[CH:8]=[C:3]([O:2][CH3:1])[C:4]=12

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67207321tert-butyl 2-{[4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-3-yl]methyl}-2,7-diazaspiro[3.5]nonane-7-carboxylate

Product 1

HCID 584046483-(2,7-diazaspiro[3.5]non-2-ylmethyl)-4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 2-{[4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-3-yl]methyl}-2,7-diazaspiro[3.5]nonane-7-carboxylate (47 mg, 0.10 mmol) in dichloromethane (2 ml) was added trifluoroacetic acid (0.008 mL, 0.1 mmol). After 30 minutes, the reaction mixture was concentrated. The residue was dissolved in methanol and eluted through a bicarbonate resin cartridge (StratoSpheres SPE, PL-HCO3 MP SPE) to give 3-(2,7-diazaspiro[3.5]non-2-ylmethyl)-4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine as a solid. 1H NMR (500 MHz, DMSO-d6) δ 8.51 (s, 1H); 8.24 (s, 1H); 7.97 (s, 1H); 7.12 (s, 1H); 6.77 (s, 1H); 3.95 (s, 3H); 3.85 (s, 3H); 3.79 (s, 2H); 2.89 (s, 4H); 2.50-2.54 (m, 4H); 1.47-1.50 (m, 4H). LRMS (ESI) calculated for C20H27N6O [M+H]+, 367.3; found 367.1.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. dissolutionThe residue was dissolved in methanol
  3. washeluted through a bicarbonate resin cartridge (StratoSpheres SPE, PL-HCO3 MP SPE)

Sources & evidence

ORD record
ord-ae9b7785cb684c8594b96101617992a6
Source dataset
uspto-grants-2013_06
Patent number
US08455477B2

Reaction notes

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