Trifluoroacetic acid → Trifluoroacetic acid

Participants

Role	Name	HCID	Charge
Reactant	Trifluoroacetic acid	HCID 6422	—
Reactant	{4-[4-(2-Chloro-phenyl)-5-oxo-4,5-dihydro-3,4,7,9,9b-pentaaza-cyclopenta[a]naphthalen-8-ylamino]-phenyl}-carbamic acid tert-butyl ester	HCID 68194660	—
Solvent	Dichloromethane	HCID 6344	—
Product	Trifluoroacetic acid	HCID 6422	—
Product	2-[(4-aminophenyl)amino]-6-(2-chlorophenyl)imidazo[1,2-a]pyrimido[5,4-e]pyrimidin-5(6H)-one	HCID 68194911	—

Reaction Steps

A mixture of Example 56A (0.260 g, 0.516 mmol) and trifluoroacetic acid (0.397 mL, 5.16 mmol) in CH2Cl2 (5 mL) was stirred at 40° C. for 4 hours. The reaction mixture was concentrated and purified by HPLC (see protocol in Example 1F) to provide the title compound as a trifluoroacetic acid salt. The salt was treated with saturated aqueous NaHCO3 followed by filtration and drying to give a free base form of the title compound. 1H NMR (400 MHz, DMSO-d6) δ 3.96 (s, 2H), 7.09 (d, J=1.8 Hz, 1H), 7.38-7.23 (m, 2H), 7.66-7.52 (m, 3H), 7.76-7.69 (m, 1H), 7.96-7.91 (m, 3H), 9.16 (s, 1H), 10.73-10.68 (m, 1H). MS (ESI+) m/z 404.2 (M+H)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08710065B2
Source dataset	uspto-grants-2014_04
ORD ID	ord-2bce8c3deceb475b849cf6fd16bbf52b
Source note	uspto-grants-2014_04