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

HRID 1914898
ノート
印刷プレビュー

反応式

HRID 1914898 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028
Tetrahydrofuran
溶媒
HCID 8058Hexane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-76f2f56bb1a749e4b1e49eeac765f76b
出典データセット
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08614239B2

反応ノート

読み込み中…

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