Hydrochloric Acid → N-((S)-((S)-5,5-dimethylpyrrolidin-2-yl)(2-fluoro-4-(trifluoromethyl)phenyl)methyl)-2-(tetrahydro-2H-pyran-4-ylamino)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	Hydrochloric Acid	HCID 313	—
Reactant	Isopropanol	HCID 3776	—
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	(S)-tert-butyl 5-((S)-(2-fluoro-4-(trifluoromethyl)phenyl)(2-(tetrahydro-2H-pyran-4-ylamino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine-7-carboxamido)methyl)-2,2-dimethylpyrrolidine-1-carboxylate	HCID 86705539	—
Solvent	Dichloromethane	HCID 6344	—
Product	N-((S)-((S)-5,5-dimethylpyrrolidin-2-yl)(2-fluoro-4-(trifluoromethyl)phenyl)methyl)-2-(tetrahydro-2H-pyran-4-ylamino)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxamide	HCID 86705540	—

Reaction Steps

To a solution of 324 (0.380 g, 0.584 mmol) and DCM (5 mL). was added 6M HCl in IPA (0.973 mL, 5.84 mmol) and the reaction was stirred for 1 h and then poured into Na2CO3 and extracted with DCM. The combined organic extracts were dried (MgSO4), filtered, and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with a DCM/MeOH gradient (500:40 to 500:50) to afford 0.210 g (65.3%) of I-86: MS m/z (APCI-pos) M+1=551.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09133187B2
Source dataset	uspto-grants-2015_09
ORD ID	ord-502fa53609a34ee5bd225cdc3ebe6b47
Source note	uspto-grants-2015_09