4-{[4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-3-yl]ethynyl}pyridin-2-amine → HCID 58404739, compound

HRID 1253555Notes

Reaction equation

HRID 1253555 reaction equation
[CH3:1][O:2][C:3]1[C:4]2[N:5]([N:15]=[CH:16][C:17]=2[C:18]#[C:19][C:20]2[CH:25]=[CH:24][N:23]=[C:22]([NH2:26])[CH:21]=2)[CH:6]=[C:7]([C:9]2[CH:10]=[N:11][N:12]([CH3:14])[CH:13]=2)[CH:8]=1>C(O)C.[OH-].[OH-].[Pd+2]>[CH3:1][O:2][C:3]1[C:4]2[N:5]([N:15]=[CH:16][C:17]=2[CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][N:23]=[C:22]([NH2:26])[CH:21]=2)[CH:6]=[C:7]([C:9]2[CH:10]=[N:11][N:12]([CH3:14])[CH:13]=2)[CH:8]=1

Participants

4

Reactant 1

HCID 584047124-{[4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-3-yl]ethynyl}pyridin-2-amine

Product 1

HCID 58404739HCID 58404739, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To a solution of 4-{[4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-3-yl]ethynyl}pyridin-2-amine (8.3 mg, 0.024 mmol) in ethanol (1 ml) was added palladium hydroxide on carbon (8 mg, 5.70 μmmol, 20 wt %). The reaction system was placed under an atmosphere of hydrogen (balloon) and stirred at ambient temperature for 7 hours. The mixture was filtered through a 45 min syringe filter and washed with EtOH. The filtrate was concentrated and the residue was purified by preparative HPLC reverse phase (C-18), eluting with acetonitrile/water+0.05% TFA. The fractions containing product were combined and diluted in ethyl acetate, then washed with aqueous sodium bicarbonate and dried over sodium sulfate. The solution was filtered and concentrated under reduced pressure to afford 4-{2-[4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-3-yl]ethyl}pyridin-2-amine 1H NMR (500 MHz, CDCl3) δ 8.18 (s, 1H), 7.87 (d, 1H), 7.73 (s, 1H), 7.56-7.63 (m, 2H), 6.54 (d, 1H), 6.39 (s, 1H), 6.36 (s, 1H), 5.18 (br s, 2H), 3.97 (s, 6H), 3.15 (t, 2H), 2.86 (t, 2H). LRMS (ESI) calculated for C19H21N6O [M+H]+, 349.2; found 349.1.

Workup

  1. filtrationThe mixture was filtered through a 45 min syringe
  2. filtrationfilter
  3. washwashed with EtOH
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by preparative HPLC reverse phase (C-18)
  6. washeluting with acetonitrile/water+0.05% TFA
  7. additionThe fractions containing product
  8. additiondiluted in ethyl acetate
  9. washwashed with aqueous sodium bicarbonate
  10. dry with materialdried over sodium sulfate
  11. filtrationThe solution was filtered
  12. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3066a58d840a4cf48555be3131da63ba
Source dataset
uspto-grants-2013_06
Patent number
US08455477B2

Reaction notes

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