Sulfuric Acid → HCID 67220280, compound

HRID 1865017Notes

Reaction equation

HRID 1865017 reaction equation
S(=O)(=O)(O)O.C([O:14][CH:15]([CH3:39])[CH2:16][NH:17][C:18]1[C:19]([S:37][CH3:38])=[N:20][N:21]2[C:26]([C:27]3[C:32]([CH3:33])=[CH:31][C:30]([CH3:34])=[CH:29][C:28]=3[O:35][CH3:36])=[CH:25][CH:24]=[CH:23][C:22]=12)(=O)C1C=CC=CC=1.[BH4-].[Na+].[OH-].[Na+].O1[CH2:48][CH2:47][CH2:46][CH2:45]1>CO>[CH:47]1([CH2:48][CH:16]([NH:17][C:18]2[C:19]([S:37][CH3:38])=[N:20][N:21]3[C:26]([C:27]4[C:32]([CH3:33])=[CH:31][C:30]([CH3:34])=[CH:29][C:28]=4[O:35][CH3:36])=[CH:25][CH:24]=[CH:23][C:22]=23)[CH:15]([OH:14])[CH3:39])[CH2:45][CH2:46]1

Participants

7

Reactant 5

HCID 1118Sulfuric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 21984728HCID 21984728, compound

Product 1

HCID 67220280HCID 67220280, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Cyclopropanecarboxyaldehyde (0.047 mL) and 3 M sulfuric acid (0.21 mL) were added to a solution of 2-[7-(2-methoxy-4,6-dimethylphenyl)-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-3-yl]amino-1-methylethyl benzoate (100 mg) in tetrahydrofuran (0.7 mL) while cooling on ice, and then sodium borohydride (16 mg) was slowly added thereto at the same temperature. The mixture was stirred for 30 minutes at room temperature, and then 5 N aqueous sodium hydroxide (0.3 mL) was added while cooling on ice to make the reaction mixture basic. Methanol (2.1 mL) was added to the reaction mixture, and after heating to reflux for 1 hour, it was returned to room temperature, extraction was performed with ethyl acetate, and the extract washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:5) to obtain the title compound (80 mg) as a yellow oil.

Workup

  1. temperaturewhile cooling on ice
  2. temperaturewhile cooling on ice
  3. temperatureafter heating
  4. temperatureto reflux for 1 hour
  5. customwas returned to room temperature
  6. extractionextraction
  7. washthe extract washed with brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:5)

Sources & evidence

ORD record
ord-d72ef2aa46404e73a56cb8fc02475239
Source dataset
uspto-grants-2009_12
Patent number
US07625925B2

Reaction notes

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