Triethylamine → HCID 59625920, compound

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Reactant	(4-(Azetidin-3-yl)piperazin-1-yl)(thiazol-2-yl)methanone	HCID 59625677	—
Reactant	HCID 59625761	HCID 59625761	—
Solvent	Water	HCID 962	—
Solvent	Dichloromethane	HCID 6344	—
Product	HCID 59625920	HCID 59625920	82.4%

Reaction Steps

To a mixture of compound 5e (42.9 mg, 0.132 mmol), compound 54c (30.3 mg, 0.12 mmol), and Et3N (0.084 mL, 0.6 mmol) in CH2Cl2 (1 mL) at room temperature was added HATU (70 mg, 0.168 mmol). The reaction mixture was stirred at room temperature overnight. The mixture was diluted with CH2Cl2 and H2O, washed with aq. NaHCO3 and brine, dried over Na2SO4, filtered, and concentrated. The residue was purified by flash column chromatography (silica gel, 2-4% MeOH/EtOAc) to give Cpd 1137 (48.1 mg). 1H NMR (400 MHz, CDCl3): δ 8.32 (s, 1H), 7.94 (d, J=7.3 Hz, 2H), 7.88 (d, J=3.2 Hz, 1H), 7.74 (d, J=9.5 Hz, 1H), 7.49-7.58 (m, 3H), 7.39-7.48 (m, 2H), 4.16 (s, 3H), 4.09-4.62 (m, 6H), 3.86 (m, 2H), 3.21-3.33 (m, 1H), 2.39-2.63 (m, 4H). MS m/z (M+H+) 487.2.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08697683B2
Source dataset	uspto-grants-2014_04
ORD ID	ord-3dacd08ec4c34fc7b485823ee4c9c586
Source note	uspto-grants-2014_04