Sodium dicyanamide → HCID 178496720, compound

Participants

Role	Name	HCID	Charge
Reactant	Sodium dicyanamide	HCID 4350929	—
Reactant	((3aR,5R,6aR)-5-(((3S,4S)-3-Methoxytetrahydro-2H-pyran-4-yl)amino)octahydro-cyclopenta[c]pyrrol-3a-yl)(3-(trifluoromethyl)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl)methanone	HCID 86708896	—
Solvent	Water	HCID 962	—
Solvent	Isopropanol	HCID 3776	—
Solvent	Dichloromethane	HCID 6344	—
Product	HCID 178496720	HCID 178496720	—

Reaction Conditions

Temperature	120 °C

Reaction Steps

A mixture of Example 1 (HCl salt, 50 mg, 0.0865 mmol), sodium dicyanamide (10.32 mg, 0.116 mmol) in 5% water in i-PrOH (1.2 mL) in a sealed tube was flushed with Ar and heated at 120° C. for 5 h. After cooling to rt, the mixture was diluted with DCM, filtered and evaporated. The residue was purified by CombiFlash (eluent: 10% 7N NH3 in methanol in DCM) to give the product as a colorless gel. 1H-NMR (400 MHz, CDCl3): δ 1.54-1.92 (m, 5H), 2.37 (br. s., 1H), 2.71 (br. s., 1H), 3.07-4.23 (m, 19H), 4.66-4.96 (m, 2H), 5.80 (m, 2H), 7.73 (s, 1H), 8.71 (br. s., 1H); LC/MS: C25H32F3N7O3: m/z 536.2 (M+H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09024017B2
Source dataset	uspto-grants-2015_05
ORD ID	ord-c3a66e4e2b5b4cce9976f297355ac063
Source note	uspto-grants-2015_05