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Hydrochloric Acid → N-Cyclopropylmethyl-N-[7-[2,6-dimethoxy-4-(methoxymethyl)phenyl]-2-(methoxymethyl)pyrazolo[1,5-a]pyridin-3-yl]amine

HRID 2253388
Notes
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Reaction equation

HRID 2253388 reaction equation
[CH:1]1([CH2:4][N:5]([C:13]2[C:14]([CH2:35][O:36][CH3:37])=[N:15][N:16]3[C:21]([C:22]4[C:27]([O:28][CH3:29])=[CH:26][C:25]([CH2:30][O:31][CH3:32])=[CH:24][C:23]=4[O:33][CH3:34])=[CH:20][CH:19]=[CH:18][C:17]=23)C(=O)OC(C)(C)C)[CH2:3][CH2:2]1.Cl.[OH-].[Na+]>C(OCC)(=O)C>[CH:1]1([CH2:4][NH:5][C:13]2[C:14]([CH2:35][O:36][CH3:37])=[N:15][N:16]3[C:21]([C:22]4[C:23]([O:33][CH3:34])=[CH:24][C:25]([CH2:30][O:31][CH3:32])=[CH:26][C:27]=4[O:28][CH3:29])=[CH:20][CH:19]=[CH:18][C:17]=23)[CH2:3][CH2:2]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21084194tert-butyl N-cyclopropylmethyl-N-[7-[2,6-dimethoxy-4-(methoxymethyl)phenyl]-2-(methoxymethyl)pyrazolo[1,5-a]pyridin-3-yl]carbamate

Product 1

HCID 21084165N-Cyclopropylmethyl-N-[7-[2,6-dimethoxy-4-(methoxymethyl)phenyl]-2-(methoxymethyl)pyrazolo[1,5-a]pyridin-3-yl]amine

Reagents, catalysts & solvents 1

HCID 8857
Ethyl Acetate
Solvent

Conditions

Temperature
40 °C

Procedure

The obtained tert-butyl N-cyclopropylmethyl-N-[7-[2,6-dimethoxy-4-(methoxymethyl)phenyl]-2-(methoxymethyl)pyrazolo[1,5-a]pyridin-3-yl]carbamate was dissolved in ethyl acetate (5 mL) without purification, and then 4N hydrochloric acid (ethyl acetate solution; 10 mL) was added thereto and the reaction mixture was stirred for 30 minutes at 40° C. The reaction mixture was neutralized with a 5N aqueous sodium hydroxide solution while cooling with ice, and then the reaction mixture was extracted with ethyl acetate and the organic extract was washed with water and brine. The organic extract was dried over anhydrous magnesium sulfate and filtered, the solvent was evaporated under reduced pressure, the residue was purified by silica gel column chromatography and the title compound (95 mg) was obtained as a yellow oil from the n-hexane:ethyl acetate (2:3) fraction.

Workup

  1. temperaturewhile cooling with ice
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. extractionthe organic extract
  4. washwas washed with water and brine
  5. extractionThe organic extract
  6. dry with materialwas dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent was evaporated under reduced pressure
  9. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-92880915fc7848a2843869b0d8d410da
Source dataset
uspto-grants-2008_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07323569B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes