4-Methylmorpholine → (R)-benzyl 2-(6-chloro-3-oxo-1-tosylpyrrolo[4,3,2-de][2,6]naphthyridin-4(1H,3H,5H)-yl)-3,3-dimethylbutanoate

Participants

Role	Name	HCID	Charge
Reactant	4-Methylmorpholine	HCID 7972	—
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	HCID 58293507	HCID 58293507	—
Product	(R)-benzyl 2-(6-chloro-3-oxo-1-tosylpyrrolo[4,3,2-de][2,6]naphthyridin-4(1H,3H,5H)-yl)-3,3-dimethylbutanoate	HCID 58293527	—

Reaction Steps

Crude (R)-4-((1-(benzyloxy)-3,3-dimethyl-1-oxobutan-2-ylamino)methyl)-5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid was heated in HATU (124 mg, 0.326 mmol) and 4-methylmorpholine (82 mg, 0.814 mmol) at reflux for 3 h. The reaction mixture was subsequently concentrated and dried in vacuo to afford the title compound. [M+H] calc'd for C29H28ClN3O5S, 566; found, 566.0.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08785429B2
Source dataset	uspto-grants-2014_07
ORD ID	ord-7f859931948d45e29e58196db593a7d2
Source note	uspto-grants-2014_07