Hydroxylamine → 4-Cyano-3-(2,4-dichlorophenyl)-5-morpholin-4-yl-N-(tetrahydro-2H-pyran-2-yloxy)thiophene-2-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	Hydroxylamine	HCID 787	—
Reactant	Dimethylformamide	HCID 6228	—
Reactant	Diisopropylethylamine	HCID 81531	—
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-Cyano-3-(2,4-dichlorophenyl)-5-morpholin-4-ylthiophene-2-carboxylic acid	HCID 44155665	—
Product	4-Cyano-3-(2,4-dichlorophenyl)-5-morpholin-4-yl-N-(tetrahydro-2H-pyran-2-yloxy)thiophene-2-carboxamide	HCID 86637548	55%

Reaction Steps

4-Cyano-3-(2,4-dichlorophenyl)-5-morpholin-4-ylthiophene-2-carboxylic acid (0.080 g, 0.21 mmol), HATU (0.095 g, 0.25 mmol), and diisopropylethylamine (0.073 mL, 0.42 mmol) were dissolved in DMF (2 mL) and stirred for 30 minutes. O-Tetrahydropyran-2-yl)hydroxylamine (0.049 g, 0.42 mmol) was added and the mixture was stirred at room temperature. After 30 minutes, LCMS showed complete conversion. Reaction was quenched by addition of water (5 mL) and the precipitate was filtered off, washed with water (2 mL) and hexane (5 mL) and dried to afford the title compound (0.055 g, 55%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09029411B2
Source dataset	uspto-grants-2015_05
ORD ID	ord-6e2604004e0f4aaf82d86d57b695d067
Source note	uspto-grants-2015_05