Diisopropylethylamine → N-[6-(1H-Indol-4-yl)-1H-indazol-4-yl]-4-methyl-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-Methylmorpholine-2-carboxylic acid hydrochloride	HCID 45480217	—
Reactant	6-(1H-indol-4-yl)-1H-indazol-4-amine	HCID 58268019	—
Solvent	Dimethylformamide	HCID 6228	—
Product	N-[6-(1H-Indol-4-yl)-1H-indazol-4-yl]-4-methyl-2-morpholinecarboxamide	HCID 44540403	—

Reaction Steps

4-Methyl-2-morpholinecarboxylic acid hydrochloride (40 mg, 0.22 mmol) was treated with HATU (84 mg, 0.22 mmol) in DMF (0.250 mL) and DIPEA (0.069 mL, 0.40 mmol). The mixture was shaken for five minutes prior to treatment with 6-(1H-indol-4-yl)-1H-indazol-4-amine (25 mg, 0.1 mmol) in DMF (0.25 mL). Reaction mixture was left to stand at room temperature for 18 hrs. Solvent was removed in vacuo and the product re-dissolved in chloroform (0.3 mL) prior to application on to a pre-conditioned (methanol then chloroform) NH2 cartridge (0.5 g). Product was eluted after 2 hr with ethyl acetate/methanol (1:1, 3 mL), and concentrated under a stream of nitrogen using blow down apparatus. Purification by MDAP (Method D) afforded the title compound.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08536169B2
Source dataset	uspto-grants-2013_09
ORD ID	ord-e1a17f80b77044f189168fe7f2dbb1e1
Source note	uspto-grants-2013_09