1-Hydroxybenzotriazole → 2-amino-N-(1-(1-oxo-4-phenyl-1H-isochromen-3-yl)ethyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 2733084	—
Reactant	2-Aminopyrazolo[1,5-A]pyrimidine-3-carboxylic acid	HCID 71742944	—
Reactant	3-(1-aminoethyl)-4-phenyl-1H-isochromen-1-one hydrochloride	HCID 118131463	—
Solvent	Dichloromethane	HCID 6344	—
Product	2-amino-N-(1-(1-oxo-4-phenyl-1H-isochromen-3-yl)ethyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide	HCID 118131200	28.3%

Reaction Steps

3-(1-aminoethyl)-4-phenyl-1H-isochromen-1-one hydrochloride (intermediate E2, 50 mg, 0.166 mmol), 2-aminopyrazolo[1,5-a]pyrimidine-3-carboxylic acid (32.5 mg, 0.182 mmol), HOBt (30.4 mg, 0.199 mmol), HBTU (17.25 mg, 0.033 mmol) and DIPEA (61.0 μl, 0.349 mmol) were reacted in DCM (1 ml) at RT for 18 hrs. The crude was purified via reverse phase chromatography with a Biotage C18 30 g SNAP column (Phase A, water 95%, ACN 5%, formic acid 0.1%); Phase B ACN 95%, water 5%, formic acid 0.1%) to give the title compound (20 mg, 28%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09321776B2
Source dataset	uspto-grants-2016_04
ORD ID	ord-9f27113e43bb4a8d98415ea5bcac342c
Source note	uspto-grants-2016_04