2-Dimethylaminopyridine → 3-(4-Tert-butoxy-phenyl)-2-{[7-cyclohexyl-6-(4-fluoro-phenyl)-pyrazolo[1,5-alpha]pyrimidine-3-carbonyl]-amino}-propionic acid tert-butyl ester

Participants

Role	Name	HCID	Charge
Reactant	2-Dimethylaminopyridine	HCID 21885	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Reactant	7-Cyclohexyl-6-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid	HCID 15958132	—
Reactant	(S)-tert-Butyl 2-amino-3-(4-(tert-butoxy)phenyl)propanoate hydrochloride	HCID 16219019	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	3-(4-Tert-butoxy-phenyl)-2-{[7-cyclohexyl-6-(4-fluoro-phenyl)-pyrazolo[1,5-alpha]pyrimidine-3-carbonyl]-amino}-propionic acid tert-butyl ester	HCID 69707174	—

Reaction Steps

To a solution of 15.0 mg (0.044 mmol) of 7-cyclohexyl-6-(4-fluoro-phenyl)-pyrazolo[1,5-α]pyrimidine-3-carboxylic acid in 2 mL of dimethylformamide (DMF) was added 0.019 mL (0.132 mmol) of diisopropylethylamine (DIEA), a few crystals of dimethylaminopyridine (DMAP cat), 17.4 mg (0.053 mmol) of H-Tyr(tBu)-OtBu.HCl, followed by 20 mg (0.053 mmol) of HATU, and the resulting mixture was stirred at rt overnight. The reaction mixture was diluted with ethyl acetate, washed with 0.1 N sodium hydroxide solution (2 times) and brine. The separated organic layer was dried over sodium sulfate and concentrated to give 3-(4-tert-butoxy-phenyl)-2-{[7-cyclohexyl-6-(4-fluoro-phenyl)-pyrazolo[1,5-α]pyrimidine-3-carbonyl]-amino}-propionic acid tert-butyl ester, which was used without any further purification in the next step.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07196111B2
Source dataset	uspto-grants-2007_03
ORD ID	ord-4bdc752511de4d00a8d6bd3cda847ed0
Source note	uspto-grants-2007_03