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

HRID 1024554Notes

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-2117337c1cfd481e8789c020e9848650
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722925B2

Reaction notes

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