Diisopropylethylamine → HCID 178436937, compound

https://huagongshe.com/reaction/2038669

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Sodium Bicarbonate	HCID 516892	—
Reactant	Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 2733084	—
Reactant	5-(2-Fluorophenoxy)-2-pyrazinecarboxylic acid	HCID 46318251	—
Reactant	5-Ethyl-2-fluoro-4-[3-(4,5,6,7-tetrahydro-1H-imidazol[4,5-c]pyridin-2-yl)-1H-indazol-6-yl]-phenol trihydrobromide salt	HCID 178419240	—
Solvent	Dimethylformamide	HCID 6228	—
Product	HCID 178436937	HCID 178436937	17.5%

Reaction Steps

To a solution of 5-(2-fluoro-phenoxy)-pyrazine-2-carboxylic acid (Preparation 45, 19 mg, 80 μmol) in DMF (1 mL) was added HBTU (32 mg, 85 μmol) and the resulting reaction mixture was stirred at room temperature for 30 minutes. 5-Ethyl-2-fluoro-4-[3-(4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridin-2-yl)-1H-indazol-6-yl]-phenol trihydrobromide salt (Preparation 25, 50 mg, 80 μmol) and DIPEA (56 μL, 320 μmol) were added and stirring was continued at room temperature for 18 hours. Saturated aqueous sodium hydrogen carbonate solution (5 mL) was added to the reaction mixture. The resulting solid was collected by filtration and washed with further saturated aqueous sodium hydrogen carbonate solution. The crude material was purified by HPLC Method B to afford 8.3 mg of the title compound.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08575336B2
Source dataset	uspto-grants-2013_11
ORD ID	ord-812291c2bb3d4c5b92a9fc60e4035838
Source note	uspto-grants-2013_11