Water → HCID 57732211、化合物

HRID 401746

反応式

HRID 401746 の反応式
I[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[S:13][CH:14]=[CH:15][N:16]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[S:17]1[CH:21]=[CH:20][CH:19]=[C:18]1[CH2:22][NH2:23].[C:24](=O)([O-])[O-:25].[Na+].[Na+].O.C(=O)([O-])[O-]>Cl.C(=[Mo](=C=O)(=C=O)(=C=O)(=C=O)=C=O)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[S:13]1[CH:14]=[CH:15][N:16]=[C:12]1[NH:11][S:8]([C:5]1[CH:6]=[CH:7][C:2]([C:24]([NH:23][CH2:22][C:18]2[S:17][CH:21]=[CH:20][CH:19]=2)=[O:25])=[CH:3][CH:4]=1)(=[O:10])=[O:9]

参加物

9

反応物 5

HCID 962WaterHCID 10340Sodium CarbonateHCID 19660Carbonate IonHCID 34005(2-Thienylmethyl)amineHCID 10193184-Iodo-N-(thiazol-2-yl)benzenesulfonamide

生成物 1

HCID 57732211HCID 57732211、化合物

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 178521658HCID 178521658、化合物触媒HCID 313Hydrochloric Acid溶媒

実験手順

4-Iodo-N-1,3-thiazol-2-ylbenzenesulfonamide (Preparation 98, 200 mg, 0.5 mmol), thiophene-2-methanamine (280 uL, 2.7 mmol), hexacarbonylmolybdenum (70 mg, 0.3 mmol), palladium(II) acetate (6 mg, 0.03 mmol), and sodium carbonate (170 mg, 1.6 mmol) in water (1.1 mL, 61 mmol) was heated 30 min at 110° C. in the microwave. The reaction mixture was diluted with 1 N HCl and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was dissolved in methylene chloride/MeOH and MP-Carbonate (2.73 mmol/g loading; 1.0 g, 2.73 mmol) was added. After stirring 1 h, LC/MS analysis indicated complete capture of the target compound. The resin was washed with methylene chloride then stirred in 8:1 methylene chloride/AcOH. LC/MS analysis indicated the target compound was released from the resin (not quantified). The material was further purified on the Isco (12 g SiO2, ethyl acetate to 4:1 ethyl acetate-MeOH).

後処理

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. dissolutionThe residue was dissolved in methylene chloride/MeOH
  7. washThe resin was washed with methylene chloride
  8. stirringthen stirred in 8:1 methylene chloride/AcOH
  9. customThe material was further purified on the Isco (12 g SiO2, ethyl acetate to 4:1 ethyl acetate-MeOH)

出典と根拠

ORDレコード
ord-3bbfcf8b344b4897a6009febe1fcff52
出典データセット
uspto-grants-2014_06
特許番号
US08741934B2

関連ノート

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