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Methanesulfonyl chloride → 2-(4-Fluorophenyl)-3-(methylcarbamoyl)-6-(n-(methylsulfonyl)methylsulfonamido)benzofuran-5-yl trifluoromethanesulfonate

HRID 1025063
ノート
印刷プレビュー

反応式

HRID 1025063 の反応式
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[F:6][C:7]([F:34])([F:33])[S:8]([O:11][C:12]1[C:13]([NH2:32])=[CH:14][C:15]2[O:19][C:18]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)=[C:17]([C:27](=[O:30])[NH:28][CH3:29])[C:16]=2[CH:31]=1)(=[O:10])=[O:9].CCN(C(C)C)C(C)C>C(Cl)Cl.CCOC(C)=O>[F:34][C:7]([F:6])([F:33])[S:8]([O:11][C:12]1[C:13]([N:32]([S:2]([CH3:1])(=[O:4])=[O:3])[S:2]([CH3:1])(=[O:4])=[O:3])=[CH:14][C:15]2[O:19][C:18]([C:20]3[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=3)=[C:17]([C:27](=[O:30])[NH:28][CH3:29])[C:16]=2[CH:31]=1)(=[O:10])=[O:9]
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 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 592755966-Amino-2-(4-fluorophenyl)-3-(methylcarbamoyl)benzofuran-5-yl trifluoromethanesulfonate

生成物 1

HCID 592754422-(4-Fluorophenyl)-3-(methylcarbamoyl)-6-(n-(methylsulfonyl)methylsulfonamido)benzofuran-5-yl trifluoromethanesulfonate収率 82%

試薬・触媒・溶媒 2

HCID 6344
Dichloromethane
溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

Methanesulfonyl chloride (146 μL, 1.873 mmol) was added to a stirring solution of 6-amino-2-(4-fluorophenyl)-3-(methylcarbamoyl)benzofuran-5-yl trifluoromethanesulfonate (270 mg, 0.624 mmol) and DIEA (500 μL, 2.86 mmol) in DCM (6.3 mL) at 25° C. It was allowed to stir for 1 hour and then diluted with EtOAc and washed with sat NaHCO3, and sat NaCl. The organic phase was dried over Na2SO4, filtered and concentrated. It was purified on silica gel (Biotage, EtOAc/hexanes gradient, fraction collection at λ=254 nm) to give the titled compound (300 mg, 82%). LC-MS retention time: 1.49 min; m/z (MH+): 589. LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a Waters XBridge 5 u C18 4.6×50 mm column using a SPD-10AV UV-Vis detector at a detector wave length of 220 nM. The elution conditions employed a flow rate of 5 ml/min, a gradient of 100% solvent A/0% solvent B to 0% solvent A/100% solvent B, a gradient time of 2 min, a hold time of 1 min, and an analysis time of 3 min where solvent A was 5% acetonitrile/95% H2O/10 mM ammonium acetate and solvent B was 5% H2O/95% acetonitrile/10 mM ammonium acetate. MS data was determined using a Micromass Platform for LC in electrospray mode.

後処理

  1. washwashed
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customIt was purified on silica gel (Biotage, EtOAc/hexanes gradient, fraction collection at λ=254 nm)

出典と根拠

ORDレコード
ord-d76b792615424a008e7415f6bccd4656
出典データセット
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08722688B2

反応ノート

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