Ethanol → N,N-Dicyclopropylmethyl-N-[7-(2-ethoxy-4,6-dimethylphenyl)-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-3-yl]amine

HRID 9221Notes

Reaction equation

HRID 9221 reaction equation
[CH2:1](O)[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[CH:35]1([CH2:38][N:39]([CH2:60][CH:61]2[CH2:63][CH2:62]2)[C:40]2[C:41]([S:58][CH3:59])=[N:42][N:43]3[C:48]([C:49]4[C:54]([CH3:55])=[CH:53][C:52]([CH3:56])=[CH:51][C:50]=4[OH:57])=[CH:47][CH:46]=[CH:45][C:44]=23)[CH2:37][CH2:36]1>O1CCCC1.C(OCC)(=O)C.O>[CH:35]1([CH2:38][N:39]([CH2:60][CH:61]2[CH2:63][CH2:62]2)[C:40]2[C:41]([S:58][CH3:59])=[N:42][N:43]3[C:48]([C:49]4[C:54]([CH3:55])=[CH:53][C:52]([CH3:56])=[CH:51][C:50]=4[O:57][CH2:1][CH3:2])=[CH:47][CH:46]=[CH:45][C:44]=23)[CH2:36][CH2:37]1

Participants

8

Reactant 4

HCID 702EthanolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 1357235202-[3-[Di(cyclopropylmethyl)amino]-2-(methylsulfanyl)pyrazolo [1,5-a]pyridin-7-yl]-3,5-dimethylphenol

Product 1

HCID 21984767N,N-Dicyclopropylmethyl-N-[7-(2-ethoxy-4,6-dimethylphenyl)-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-3-yl]amine

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

After adding ethanol (2 μL), triphenylphosphine (15 mg) and diethyl azodicarboxylate (9 μL) to a solution of 2-[3-[di(cyclopropylmethyl)amino]-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-7-yl]-3,5-dimethylphenol (15 mg) in tetrahydrofuran (0.45 mL) under a nitrogen atmosphere, the mixture was stirred at room temperature overnight. The reaction mixture was added to water, extraction was performed with ethyl acetate, and the organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, and the title compound (3.7 mg) was obtained from the n-hexane:ethyl acetate (9:1) fraction as a yellow oil.

Workup

  1. washthe organic layer was washed with brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9482f3b28cc4406ca403d81c37c7da8b
Source dataset
uspto-grants-2006_08
Patent number
US07091215B2

Reaction notes

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