Water → N,N-Dicyclopropylmethyl-N-[7-(2-methoxy-4,6-dimethylphenyl)-2-(methylsulfinyl)pyrazolo[1,5-a]pyridin-3-yl]amine

HRID 9223Notes

Reaction equation

HRID 9223 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH:12]1([CH2:15][N:16]([CH2:38][CH:39]2[CH2:41][CH2:40]2)[C:17]2[C:18]([S:36][CH3:37])=[N:19][N:20]3[C:25]([C:26]4[C:31]([CH3:32])=[CH:30][C:29]([CH3:33])=[CH:28][C:27]=4[O:34][CH3:35])=[CH:24][CH:23]=[CH:22][C:21]=23)[CH2:14][CH2:13]1.O.C(OCC)(=O)C>ClCCl>[CH:12]1([CH2:15][N:16]([CH2:38][CH:39]2[CH2:41][CH2:40]2)[C:17]2[C:18]([S:36]([CH3:37])=[O:9])=[N:19][N:20]3[C:25]([C:26]4[C:31]([CH3:32])=[CH:30][C:29]([CH3:33])=[CH:28][C:27]=4[O:34][CH3:35])=[CH:24][CH:23]=[CH:22][C:21]=23)[CH2:13][CH2:14]1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 70297m-Chloroperbenzoic acidHCID 21984670N,N-dicyclopropylmethyl-N-[7-(2-methoxy-4,6-dimethylphenyl)-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-3-yl]amine

Product 1

HCID 21984550N,N-Dicyclopropylmethyl-N-[7-(2-methoxy-4,6-dimethylphenyl)-2-(methylsulfinyl)pyrazolo[1,5-a]pyridin-3-yl]amineYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

m-Chloroperbenzoic acid (234 mg) was added to a solution of N,N-dicyclopropylmethyl-N-[7-(2-methoxy-4,6-dimethylphenyl)-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-3-yl]amine (200 mg) in dichloromethane (10 mL) at 0° C., and the mixture was stirred for 2 hours. Water was added to the reaction mixture, extraction was performed with ethyl acetate, the extract was washed with saturated aqueous sodium hydrogencarbonate and brine and dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography (20 g), and the title compound (162 mg) was obtained from the n-hexane:ethyl acetate (1:1) fraction as a light yellow oil.

Workup

  1. washthe extract was washed with saturated aqueous sodium hydrogencarbonate and brine
  2. dry with materialdried over magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-1041e44b85e54e55bc7caa4f4b544baa
Source dataset
uspto-grants-2006_08
Patent number
US07091215B2

Reaction notes

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