Dimethylformamide → 6-Chloro-N-{(3S)-1-[(1S)-1-methyl-2-morpholin-4-yl-2-oxoethyl]-2-oxopyrrolidin-3-yl}-N-(2-morpholin-4-ylethyl)naphthalene-2-sulfonamide formate

Participants

Role	Name	HCID	Charge
Reactant	Dimethylformamide	HCID 6228	—
Reactant	Ethyl Acetate	HCID 8857	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)	HCID 77210	—
Reactant	tert-Butyl(2R)-2-((3R)-3-{[(6-chloro-2-naphthyl)sulfonyl]amino}-2-oxopyrrolidin-1-yl)propanoate	HCID 69222335	—
Solvent	Water	HCID 962	—
Product	6-Chloro-N-{(3S)-1-[(1S)-1-methyl-2-morpholin-4-yl-2-oxoethyl]-2-oxopyrrolidin-3-yl}-N-(2-morpholin-4-ylethyl)naphthalene-2-sulfonamide formate	HCID 10189365	—

Reaction Conditions

Temperature	40 °C

Reaction Steps

Example 1 (0.05 g) was dissolved in DMF (1 ml) and treated with chloroethylmorpholine hydrochloride (0.062 g) and potassium carbonate (0.093 g), and stirred at 40° C. for 2 h. The mixture was then heated at 80° C. for 8 h, cooled and treated with ethyl acetate and water. The organic extract was dried (over magnesium sulphate) and concentrated under reduced pressure. The residue was purified using mass directed preparative h.p.l.c. to give the title compound (0.018 g) as a white solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07186717B2
Source dataset	uspto-grants-2007_03
ORD ID	ord-631e041817c948b699cebb3795922f13
Source note	uspto-grants-2007_03