Water → 2-amino-6-fluoro-N-(4-(4-methylpiperazin-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	(2Z)-3-(diisopropylamino)-2-fluoro-2-propenal	HCID 14934227	—
Reactant	3,5-diamino-N-[4-(4-methylpiperazin-1-yl)-3-pyridyl]-1H-pyrazole-4-carboxamide	HCID 86720899	—
Reactant	1H-benzo[d][1,2,3]triazol-1-yl 2-amino-6-(cyanomethyl)pyrazolo[1,5-a]pyrimidine-3-carboxylate	HCID 90199892	—
Solvent	Dimethyl Sulfoxide	HCID 679	—
Product	2-amino-6-fluoro-N-(4-(4-methylpiperazin-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide	HCID 86720898	—

Reaction Conditions

Temperature	140 °C

Reaction Steps

A mixture of (Z)-3-(diisopropylamino)-2-fluoro-prop-2-enal (Tetrahedron Letters (1992), 33(3), 357-60) (22.81 mg, 0.1317 mmol), 4-methylbenzenesulfonic acid (Water (1)) (30.05 mg, 0.1580 mmol), 3,5-diamino-N-[4-(4-methylpiperazin-1-yl)-3-pyridyl]-1H-pyrazole-4-carboxamide (50 mg, 0.1580 mmol) in DMSO (1 mL)/H2O (0.5 mL) was stirred at 140° C. for 25 min. The crude mixture was purified by Fractionlynx HPLC. The aqueous fractions were combined and lyophilised to yield 2-amino-6-fluoro-N-(4-(4-methylpiperazin-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide. (10 mg, 21%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09340546B2
Source dataset	uspto-grants-2016_05
ORD ID	ord-415311000d504200a33cf2f3d274d84b
Source note	uspto-grants-2016_05