Diisopropylethylamine → HCID 58477342, compound

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	2-Amino-5-methylthiazole	HCID 351770	—
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	HCID 58477232	HCID 58477232	—
Solvent	Water	HCID 962	—
Solvent	Dimethylformamide	HCID 6228	—
Product	HCID 58477342	HCID 58477342	32.8%

Reaction Conditions

Temperature	55 °C

Reaction Steps

A mixture of 4-oxo-2-(2-(trifluoromethyl)pyridin-3-yl)-4H-chromene-8-carboxylic acid 41 (210 mg, 0.6 mmol), 5-methyl-1,3-thiazole-2-ylamine 47 (68 mg, 0.6 mmol), HATU (274 mg, 0.72 mmol), and DIPEA (155 mg, 1.2 mmol) in DMF (4 mL) was stirred at 55° C. for 12 h. The reaction mixture was poured into H2O (25 mL) and extracted with ethyl acetate. The organic layer was concentrated and purified by flash chromatography to give Compound 305 (85 mg, 32% yield). MS (ESI) calcd for C20H12F3N3O3S: 431.06. found: 432 [M+H].

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08987258B2
Source dataset	uspto-grants-2015_03
ORD ID	ord-10dc9d1f60df48fc9c365261cbb5f82f
Source note	uspto-grants-2015_03