Ethyl Acetate → HCID 178419018, compound

HRID 9219Notes

Reaction equation

HRID 9219 reaction equation
C1(C[N:5]([C:15]2[C:16]([S:34][CH3:35])=[N:17][N:18]3[C:23]([C:24]4[C:29]([CH3:30])=[CH:28][C:27]([CH3:31])=[CH:26][C:25]=4[O:32][CH3:33])=[CH:22][CH:21]=[CH:20][C:19]=23)[CH2:6][C:7]2[C:8]([O:13]C)=[N:9][CH:10]=[CH:11][CH:12]=2)CC1.Cl.C(O[CH2:41][CH3:42])(=O)C.C(=O)([O-])O.[Na+].[C:48](OCC)(=O)[CH3:49]>C(O)C>[CH:41]1([CH2:42][CH:6]([NH:5][C:15]2[C:16]([S:34][CH3:35])=[N:17][N:18]3[C:23]([C:24]4[C:29]([CH3:30])=[CH:28][C:27]([CH3:31])=[CH:26][C:25]=4[O:32][CH3:33])=[CH:22][CH:21]=[CH:20][C:19]=23)[C:7]2[C:8]([OH:13])=[N:9][CH:10]=[CH:11][CH:12]=2)[CH2:49][CH2:48]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 21866389Hydrogen chloride-ethyl acetateHCID 21984581HCID 21984581, compound

Product 1

HCID 178419018HCID 178419018, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

After dissolving N-cyclopropylmethyl-N-[7-(2-methoxy-4,6-dimethylphenyl)-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-3-yl]-N-[(2-methoxy-3-pyridyl)methyl]amine (63 mg) in ethanol (1 mL), a 4 N hydrochloric acid/ethyl acetate solution (1 mL) was added at room temperature and the mixture was heated to reflux for 3 hours. Saturated aqueous sodium hydrogencarbonate was added to the reaction mixture for neutralization while cooling on ice, and extraction was performed with ethyl acetate. The obtained organic layer was washed with water and dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate) to obtain the title compound (49 mg) as white crystals.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 3 hours
  3. temperaturewhile cooling on ice, and extraction
  4. washThe obtained organic layer was washed with water
  5. dry with materialdried over magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-c733e954d17546e38092c836e263de83
Source dataset
uspto-grants-2006_08
Patent number
US07091215B2

Reaction notes

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