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Ethyl Acetate → Cyclopropanesulfonic acid [4,5-difluoro-6-(2-fluoro-4-iodo-phenylamino)-benzooxazol-7-yl]-amide

HRID 1914898
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1914898
[K].[CH:2]1([S:5]([N:8]2[C:12]3[C:13]4[O:17][CH:16]=[N:15][C:14]=4[C:18]([F:21])=[C:19]([F:20])[C:11]=3[N:10]([C:22]3[CH:27]=[CH:26][C:25]([I:28])=[CH:24][C:23]=3[F:29])C2=O)(=[O:7])=[O:6])[CH2:4][CH2:3]1.C(OCC)(=O)C>C1COCC1.CCCCCC>[F:21][C:18]1[C:14]2[N:15]=[CH:16][O:17][C:13]=2[C:12]([NH:8][S:5]([CH:2]2[CH2:4][CH2:3]2)(=[O:7])=[O:6])=[C:11]([NH:10][C:22]2[CH:27]=[CH:26][C:25]([I:28])=[CH:24][C:23]=2[F:29])[C:19]=1[F:20]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 8857Ethyl AcetateHCID 5462222PotassiumHCID 672370348-Cyclopropanesulfonyl-4,5-difluoro-6-(2-fluoro-4-iodo-phenyl)-6,8-dihydro-imidazo[4',5':3,4]benzo[1,2-d]oxazol-7-one

Produkt 1

HCID 53241452Cyclopropanesulfonic acid [4,5-difluoro-6-(2-fluoro-4-iodo-phenylamino)-benzooxazol-7-yl]-amideAusbeute 29,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028
Tetrahydrofuran
Lösungsmittel
HCID 8058HexaneLösungsmittel

Versuchsvorschrift

Potassium trimethylsilonolate (29 mg, 0.182 mmol) was added to a solution of 8-cyclopropanesulfonyl-4,5-difluoro-6-(2-fluoro-4-iodo-phenyl)-6,8-dihydro-imidazo[4′,5′:3,4]benzo[1,2-d]oxazol-7-one (I-19a: 65 mg, 0.121 mmol) in THF (5 mL) and the resulting mixture was stirred at room temperature for 1 hour. The reaction was monitored by TLC (50% ethyl acetate in hexane). The reaction mixture was concentrated and the concentrate was dissolved in water, acidified with 2N HCl and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous Na2SO4 and concentrated to afford the crude product. Purification by column chromatography on silica gel (25-35% ethyl acetate in hexane) afforded 18 mg of the product (29.5% yield).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe concentrate was dissolved in water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated
  7. customto afford the crude product
  8. customPurification by column chromatography on silica gel (25-35% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-76f2f56bb1a749e4b1e49eeac765f76b
Quelldatensatz
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08614239B2

Notizen zur Reaktion

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