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

HRID 1914898
Notes
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Reaction equation

HRID 1914898 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 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

Product 1

HCID 53241452Cyclopropanesulfonic acid [4,5-difluoro-6-(2-fluoro-4-iodo-phenylamino)-benzooxazol-7-yl]-amideYield 29.5%

Reagents, catalysts & solvents 2

HCID 8028
Tetrahydrofuran
Solvent
HCID 8058HexaneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-76f2f56bb1a749e4b1e49eeac765f76b
Source dataset
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08614239B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes