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Hydrochloric Acid → 8-[5-({[5-Methyl-1-(4-methylphenyl)-1H-pyrazol-4-yl]carbonyl}amino)pyridin-2-yl]-1,4-dioxaspiro[4.5]decane-8-carboxylic acid ethyl ester

HRID 1748621
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1748621
S(Cl)(Cl)=O.[CH3:5][C:6]1[N:10]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)[N:9]=[CH:8][C:7]=1[C:18]([OH:20])=O.[CH2:21]([O:23][C:24]([C:26]1([C:36]2[CH:41]=[CH:40][C:39]([NH2:42])=[CH:38][N:37]=2)[CH2:35][CH2:34][C:29]2([O:33][CH2:32][CH2:31][O:30]2)[CH2:28][CH2:27]1)=[O:25])[CH3:22].Cl>C1(C)C=CC=CC=1.N1C=CC=CC=1.CN(C)C=O>[CH2:21]([O:23][C:24]([C:26]1([C:36]2[CH:41]=[CH:40][C:39]([NH:42][C:18]([C:7]3[CH:8]=[N:9][N:10]([C:11]4[CH:12]=[CH:13][C:14]([CH3:17])=[CH:15][CH:16]=4)[C:6]=3[CH3:5])=[O:20])=[CH:38][N:37]=2)[CH2:35][CH2:34][C:29]2([O:30][CH2:31][CH2:32][O:33]2)[CH2:28][CH2:27]1)=[O:25])[CH3:22]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 27695835-methyl-1-(4-methylphenyl)-1H-pyrazole-4-carboxylic acidHCID 866924568-(5-Aminopyridin-2-yl)-1,4-dioxaspiro[4,5]decane-8-carboxylic acid ethyl ester

Produkt 1

HCID 866925638-[5-({[5-Methyl-1-(4-methylphenyl)-1H-pyrazol-4-yl]carbonyl}amino)pyridin-2-yl]-1,4-dioxaspiro[4.5]decane-8-carboxylic acid ethyl ester
Ausbeute 81,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1049PyridineLösungsmittelHCID 1140TolueneLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Thionyl chloride (185 mg) and N,N-dimethylformamide (catalytic amounts) were added at room temperature to a solution of 5-methyl-1-(4-methylphenyl)-1H-pyrazole-4-carboxylic acid (210 mg) described in Reference Example 4 in toluene (3.0 ml) and stirred at 80° C. for an hour. The solvent and excess amounts of thionyl chloride were evaporated. The resulting reaction mixture of a pyridine solution (1.5 ml) was added to a solution of 8-(5-aminopyridin-2-yl)-1,4-dioxaspiro[4.5]decane-8-carboxylic acid ethyl ester (312 mg) in pyridine (1.8 ml) and stirred at 40° C. for an hour. After the reaction, the reaction solution was cooled to room temperature, adjusted to pH 4-5 by the addition of 1N hydrochloric acid aqueous solution and extracted with ethyl acetate. The organic layer was washed with 1N hydrochloric acid aqueous solution, dried over anhydrous sodium sulfate and concentrated to give the titled compound (400 mg) as a white solid.

Aufarbeitung

  1. customThe solvent and excess amounts of thionyl chloride were evaporated
  2. customThe resulting reaction mixture of a pyridine solution (1.5 ml)
  3. stirringstirred at 40° C. for an hour
  4. customAfter the reaction
  5. temperaturethe reaction solution was cooled to room temperature
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with 1N hydrochloric acid aqueous solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-cb7edc3cbfb346018906ab5926bb8973
Quelldatensatz
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09150555B2

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