Diisopropylethylamine → 4-Acetyl-N-[6-(1H-indol-4-yl)-1H-indazol-4-yl]-2-morpholinecarboxamide

Participants

Role	Name	HCID	Charge
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-Acetylmorpholine-2-carboxylic acid	HCID 20598078	—
Reactant	6-(1H-indol-4-yl)-1H-indazol-4-amine	HCID 58268019	—
Solvent	Dimethylformamide	HCID 6228	—
Product	4-Acetyl-N-[6-(1H-indol-4-yl)-1H-indazol-4-yl]-2-morpholinecarboxamide	HCID 44540311	30.1%

Reaction Steps

To a solution of HATU (0.107 g, 0.28 mmol) in dry DMF (3 ml) was added 4-acetyl-2-morpholinecarboxylic acid (0.05 g, 0.282 mmol). DIPEA (0.098 ml, 0.56 mmol) was added and the mixture was left to stand for 10 min. 6-(1H-indol-4-yl)-1H-indazol-4-amine (0.04 g, 0.14 mmol), dissolved in dry DMF (3 ml) was added and the solution was left to stand at room temperature for 20 hr. DMF was removed by blow down under a stream of nitrogen, then the residue was dissolved and purified by Mass Directed AutoPrep Method B. The solvent was removed in vacuo and product dried in a vacuum oven at 50° C. overnight to give the title compound as a brown oil (17 mg).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08536169B2
Source dataset	uspto-grants-2013_09
ORD ID	ord-9c46e66f17024e1990e7244b6b765a50
Source note	uspto-grants-2013_09