Hydrochloric Acid → 7-Cyclohexyl-6-[4-(3-methoxyphenyl)phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylic acid

HRID 460691Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 460691
C([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]2[C:14]([CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)=[C:13]([C:21]3[CH:26]=[CH:25][C:24]([C:27]4[CH:32]=[CH:31][CH:30]=[C:29]([O:33][CH3:34])[CH:28]=4)=[CH:23][CH:22]=3)[CH:12]=[N:11][C:10]=12)=[O:5])C.[Li+].[OH-].Cl>O1CCCC1>[CH:15]1([C:14]2[N:9]3[N:8]=[CH:7][C:6]([C:4]([OH:5])=[O:3])=[C:10]3[N:11]=[CH:12][C:13]=2[C:21]2[CH:22]=[CH:23][C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([O:33][CH3:34])[CH:28]=3)=[CH:25][CH:26]=2)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 691552937-Cyclohexyl-6-(3'-methoxy-biphenyl-4-yl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid ethyl ester

Produkt 1

HCID 159581197-Cyclohexyl-6-[4-(3-methoxyphenyl)phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylic acidAusbeute 34,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 47 mg (0.103 mmol) of 7-cyclohexyl-6-(3′-methoxy-biphenyl-4-yl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid ethyl ester in 3 mL of tetrahydrofuran was added 0.62 mL (0.62 mmol) of 1 M LiOH solution, and the resulting mixture was heated at reflux overnight. The reaction mixture was then acidified with 1 M HCl solution to pH=2, and extracted with ethyl acetate. The combined organic extracts were dried over sodium sulfate, and concentrated to give a residue which was purified via reverse-phase chromatography to afford (after lyophilization) 15 mg (34% yield) of 7-cyclohexyl-6-(3′-methoxy-biphenyl-4-yl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (446) as a solid (90% purity) as indicated by 1H NMR; LC-MS—calcd for C26H25N3O3 [M++H]+: 428.19, found: 428.2.

Aufarbeitung

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux overnight
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic extracts were dried over sodium sulfate
  5. concentrationconcentrated
  6. customto give a residue which
  7. customwas purified via reverse-phase chromatography

Quellen und Nachweise

ORD-Eintrag
ord-619ed55f65e84eaab43412e7f8e5501e
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07196111B2

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