Methanesulfonic Acid → 6-Chloro-3-(2-(1,1,1,3,3,3-hexafluoropropan-2-ylamino)-3,4-dioxocyclobut-1-enylamino)-2-hydroxy-n-methoxy-n-methylbenzenesulfonamide

HRID 516908

Reaktionsgleichung

Reaktionsgleichung von HRID 516908
[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.[CH:26]([NH2:35])([C:31]([F:34])([F:33])[F:32])[C:27]([F:30])([F:29])[F:28].CS(O)(=O)=O>C1COCC1>[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:35][CH:26]([C:31]([F:34])([F:33])[F:32])[C:27]([F:30])([F:29])[F:28])=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 6395Methanesulfonic AcidHCID 122246671,1,1,3,3,3-Hexafluoropropan-2-amineHCID 568442936-chloro-3-(2-ethoxy-3,4-dioxo-cyclobut-1-enylamino)-2-hydroxy-N-methoxy-N-methyl-benzenesulfonamide2×

Produkt 1

HCID 446291516-Chloro-3-(2-(1,1,1,3,3,3-hexafluoropropan-2-ylamino)-3,4-dioxocyclobut-1-enylamino)-2-hydroxy-n-methoxy-n-methylbenzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

6-Chloro-3-(2-ethoxy-3,4-dioxocyclobut-1-enylamino)-2-hydroxy-N-methoxy-N-methylbenzenesulfonamide (Intermediate A) (50 mg, 0.102 mmol) and 1,1,1,3,3,3-hexafluoroisopropylamine (34.0 mg, 0.203 mmol) were dissolved THF (1 ml). To the solution was added methanesulfonic acid (7 μl, 0.108 mmol) and the resultant mixture was heated at 50° C. overnight (˜18 hr). The solution was concentrated in vacuo and the residue was re-dissolved in DMSO (900 μl). The solution was transferred to a HPLC vial and purified using mass-directed prep system using 50-98% acetonitrile in water (0.1% TFA). The solvent was removed from the purified fraction in vacuo. The residue was re-dissolved in MeOH the solvent was removed in vacuo to afford the title compound as an orange solid;

Aufarbeitung

  1. concentrationThe solution was concentrated in vacuo
  2. dissolutionthe residue was re-dissolved in DMSO (900 μl)
  3. custompurified
  4. customThe solvent was removed from the purified fraction in vacuo
  5. dissolutionThe residue was re-dissolved in MeOH the solvent
  6. customwas removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-dc28ed8339a8470485c519b3adcae31f
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09115087B2

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