Syntheses of 1-substituted-3-aminopyrazoles

Tetrahedron Letters

Volumn 51, Issue 52, 2010, Pages 6799-6801

  Ji, Nan ^a   Meredith, Erik ^a   Liu, Donglei ^a   Adams, Christopher M ^a   Artman III, Gerald D ^a   Jendza, Keith C ^a   Ma, Fupeng ^a   Mainolfi, Nello ^a   Powers, James J ^a   Zhang, Chun ^a  

^a NOVARTIS INSTITUTES FOR BIOMEDICAL RESEARCH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 AMINOPYRAZOLE; PYRAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SUBSTITUTION REACTION;

EID: 78650690813     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.10.073     Document Type: Article

References (19)

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18. 3. An NMR analysis of this solution was performed. Peaks from the regioisomers were identified and ratio of regioisomers was calculated based on integration values.
19. 4), filtered, and concentrated. The residue was used directly in the next step without further purification. A solution of crude 7-hydroxy-4,4-dimethyl-3-oxoheptanenitrile (12b) (3.00 g, 17.7 mmol), hydrazine (0.85 mL, 26.6 mmol) in MeOH (25 mL) was heated at 80 °C. After 16 h, another aliquot of hydrazine (0.85 mL, 26.6 mmol) was added and heating was continued for an additional 8 h. The solution was then concentrated and purified via flash column chromatography (10% MeOH-DCM) to provide 13b (2.75 g, 38%, two-steps). To a solution of 4-(5-amino-2H-pyrazol-3-yl)-4-methyl-pentan-1-ol (5.00 g, 27.3 mmol) in THF (150 mL) at rt was added thionyl chloride (10.0 mL, 136 mmol).