Diisopropylethylamine → HCID 44476576, compound

https://huagongshe.com/reaction/2192526

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	6-(2,2,2-Trifluoroethoxy)pyridine-3-carboxylic acid	HCID 2781028	—
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 178513273	HCID 178513273	—
Solvent	Dimethylformamide	HCID 6228	—
Product	HCID 44476576	HCID 44476576	14.1%

Reaction Conditions

Temperature	120 °C

Reaction Steps

6-[(2,2,2-Trifluoroethyl)oxy]-3-pyridinecarboxylic acid (Fluorochem; 130 mg, 0.642 mmol) was stirred in DMF (1 ml) with HATU (244 mg, 0.642 mmol) and DIPEA (0.28 ml, 1.605 mmol) at room temperature for 30 mins before adding a solution of N-hydroxy-5-isoquinolinecarboximidamide (D1, 100 mg, 0.535 mmol) in DMF (1 ml). The resulting mixture was heated to 120° C. for 30 mins in a Biotage Initiator microwave. The solvent was removed under vacuum, and the residue was purified by column chromatography on silica, eluting with 0-60% ethyl acetate in cyclohexane. The relevant fractions were combined and concentrated under vacuum to give the title compound as a white solid (28 mg).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08329730B2
Source dataset	uspto-grants-2012_12
ORD ID	ord-98b375d79e3b406e8ceb335a330395c0
Source note	uspto-grants-2012_12