6-chloro-3-(2-ethoxy-3,4-dioxo-cyclobut-1-enylamino)-2-hydroxy-N-methoxy-N-methyl-benzenesulfonamide → HCID 86658405, compound

HRID 2192712Notes

Reaction equation

[Cl:1][C:2]1[C:7]([S:8]([N:11]([O:13][CH3:14])[CH3:12])(=[O:10])=[O:9])=[C:6]([OH:15])[C:5]([NH:16][C:17]2[C:20](=[O:21])[C:19](=[O:22])[C:18]=2OCC)=[CH:4][CH:3]=1.[O:26]1[CH2:30][CH2:29][CH2:28][CH:27]1[C@H:31]([NH2:34])[CH2:32][CH3:33]>CC#N>[Cl:1][C:2]1[C:7]([S:8]([N:11]([O:13][CH3:14])[CH3:12])(=[O:9])=[O:10])=[C:6]([OH:15])[C:5]([NH:16][C:17]2[C:20](=[O:21])[C:19](=[O:22])[C:18]=2[NH:34][C@@H:31]([CH:27]2[CH2:28][CH2:29][CH2:30][O:26]2)[CH2:32][CH3:33])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a stirred solution of 6-chloro-3-(2-ethoxy-3,4-dioxocyclobut-1-enylamino)-2-hydroxy-N-methoxy-N-methylbenzenesulfonamide (Intermediate A) (500 mg, 1.279 mmol) in MeCN was added TEA (1.783 ml, 12.79 mmol) and (R)-1-(tetrahydro-furan-2-yl)-propylamine (1 g, 7.74 mmol) (Intermediate DA). The reaction mixture was heated to 70° C. over night. The reaction mixture was evaporated to dryness. The residue was dissolved in DCM and washed with 0.1M aqueous HCl. The organic layer was dried over MgSO4, filtered and evaporated to dryness. The diastereomers were separated by Supercritical fluid chromatography according to the following conditions:

Workup

customThe reaction mixture was evaporated to dryness
dissolutionThe residue was dissolved in DCM
washwashed with 0.1M aqueous HCl
dry with materialThe organic layer was dried over MgSO4
filtrationfiltered
customevaporated to dryness
customThe diastereomers were separated by Supercritical fluid chromatography

Sources & evidence

ORD record: ord-e3bbcb35225444e2a1f0393ce6018c15
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08329754B2

Reaction notes

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