4-Methylmorpholine → ((S)-1-{[(3,5-Diamino-6-chloro-pyrazine-2-carbonyl)-amino]-methyl}-butyl)-carbamic acid tert-butyl ester

Participants

Role	Name	HCID	Charge
Reactant	4-Methylmorpholine	HCID 7972	—
Reactant	3,5-Diamino-6-chloro-pyrazine acid	HCID 6452119	—
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	((S)-1-Aminomethyl-butyl)-carbamic acid tert-butyl ester	HCID 86651886	—
Solvent	Dimethylformamide	HCID 6228	—
Product	((S)-1-{[(3,5-Diamino-6-chloro-pyrazine-2-carbonyl)-amino]-methyl}-butyl)-carbamic acid tert-butyl ester	HCID 86651887	—

Reaction Steps

A mixture of ((S)-1-aminomethyl-butyl)-carbamic acid tert-butyl ester (1.70 g, 8.40 mmol), 3,5-diamino-6-chloro-pyrazine-2-carboxylic acid (1.59 g, 8.43 mmol), N-methylmorpholine (3.8 mL, 34.5 mmol) and HATU (3.2 g, 8.42 mmol) in anhydrous DMF (50 mL) is stirred at RT for 16 h. The reaction mixture is concentrated in vacuo and the resulting residue is purified by column chromatography (basic alumina, MeOH:DCM) to afford the title compound as yellow solid. [M+H]+ 333.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08664228B2
Source dataset	uspto-grants-2014_03
ORD ID	ord-0cccc2e793234150be418124d328a5fa
Source note	uspto-grants-2014_03