Diisopropylethylamine → 6-Bromo-N-[6-(4-hydroxyphenyl)-1H-indazol-4-yl]-2-pyridinecarboxamide

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	6-Bromopyridine-2-carboxylic acid	HCID 593919	—
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	2-(Tetrahydro-2H-pyran-2-yl)-6-[4-(tetrahydro-2H-pyran-2-yloxy)phenyl]-2H-indazol-4-amine	HCID 58255837	—
Solvent	Dimethylformamide	HCID 6228	—
Product	6-Bromo-N-[6-(4-hydroxyphenyl)-1H-indazol-4-yl]-2-pyridinecarboxamide	HCID 135927891	—

Reaction Conditions

Temperature	70 °C

Reaction Steps

2-(Tetrahydro-2H-pyran-2-yl)-6-[4-(tetrahydro-2H-pyran-2-yloxy)phenyl]-2H-indazol-4-amine (500 mg, 1.27 mmol), 6-bromo-2-pyridinecarboxylic acid (272 mg, 1.35 mmol), HATU (531 mg, 1.35 mmol) and DIPEA (0.442 ml, 2.54 mmol) were combined in DMF (10 ml) and heated at 70° C. overnight. The solvent was removed in vacuo and the residue was purified by silica gel chromatography, eluting with DCM:MeOH:ammonia. Appropriate fractions were combined and the solvent was removed in vacuo. The residue was dissolved in Methanol (20 ml) and 4 M HCl in dioxane (2 ml) and stirred at RT for 5 days. A small amount of the reaction mixture was removed (2 ml), the solvent was removed in vacuo and the residue purified by MDAP (Method B) to give the title compound.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08163743B2
Source dataset	uspto-grants-2012_04
ORD ID	ord-de44e72d25b240a8bfec4b31305eaf2a
Source note	uspto-grants-2012_04