Diisopropylethylamine → Phenylmethyl 3-hydroxy-4-({[6-(1H-indol-4-yl)-1H-indazol-4-yl]amino}carbonyl)-1-pyrrolidinecarboxylate

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	1-N-Cbz-4-hydroxy-beta-proline	HCID 44890918	—
Reactant	6-(1H-indol-4-yl)-1H-indazol-4-amine	HCID 58268019	—
Solvent	Dimethylformamide	HCID 6228	—
Product	Phenylmethyl 3-hydroxy-4-({[6-(1H-indol-4-yl)-1H-indazol-4-yl]amino}carbonyl)-1-pyrrolidinecarboxylate	HCID 44540587	6.4%

Reaction Steps

To a solution of 4-hydroxy-1-{[(phenylmethyl)oxy]carbonyl}-3-pyrrolidinecarboxylic acid (available from Fluorochem, 59 mg, 0.22 mmol) in DMF (1 ml) was added HATU (85 mg, 0.22 mmol) and the mixture stirred for 10 mins. Then 6-(1H-indol-4-yl)-1H-indazol-4-amine (46 mg, 0.19 mmol) and DIPEA (0.065 ml, 0.37 mmol) were added and the mixture allowed to stand for 18 h at 20° C. The solvent was removed under a stream of nitrogen and the residue purified by Mass Directed Automated Preparative HPLC (Method E), to give the title compound (6 mg) as a brown solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08536169B2
Source dataset	uspto-grants-2013_09
ORD ID	ord-c870562fc785452990d4e33df5171831
Source note	uspto-grants-2013_09