Diisopropylethylamine → HCID 66832094, compound

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	5-Chloro-1H-indole-3-ethylamine monohydrochloride	HCID 2827494	—
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	Ethyl 5-((5-methyl-2-phenyloxazol-4-yl)methyl)-1,2,4-oxadiazole-3-carboxylate	HCID 66832125	—
Solvent	Water	HCID 962	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Tetrahydrofuran	HCID 8028	—
Solvent	Sodium Hydroxide	HCID 14798	—
Product	HCID 66832094	HCID 66832094	—

Reaction Steps

This compound was prepared according to method F with ethyl 5-((5-methyl-2-phenyloxazol-4-yl)methyl)-1,2,4-oxadiazole-3-carboxylate (0.075 g; 0.238 mmol) in THF (1 mL) and sodium hydroxide in water (2M, 1 mL); 2-(5-chloro-1H-indol-3-yl)ethanamine hydrochloride (0.055 g; 0.238 mmol), HATU (0.090 g; 0.238 mmol), N,N diisopropylethylamine (0.102 mL; 0.594 mmol), in DMF (3 mL). The crude mixture was purified by flash column chromatography on silica (eluent 20 to 100% ethyl acetate in heptane) to yield 0.042 (39%) of the title compound as a white solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09434722B2
Source dataset	uspto-grants-2016_09
ORD ID	ord-11af02dc78e34bd2b86157df83cc7260
Source note	uspto-grants-2016_09