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Water → N-[[6-(4-Oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]methyl]-2-thiophenecarboxamide

HRID 499473
ノート
印刷プレビュー

反応式

HRID 499473 の反応式
FC(F)(F)C(O)=O.[NH2:8][CH2:9][C:10]1[N:15]=[C:14]([C:16]2[S:17][C:18]3[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=3[C:20](=[O:22])[N:21]=2)[CH:13]=[CH:12][CH:11]=1.[C:27]1([C:32](Cl)=[O:33])[S:31][CH:30]=[CH:29][CH:28]=1.C(OCC)(=O)C.O>CN(C)C(=O)C>[O:22]=[C:20]1[C:19]2[CH:23]=[CH:24][CH:25]=[CH:26][C:18]=2[S:17][C:16]([C:14]2[N:15]=[C:10]([CH2:9][NH:8][C:32]([C:27]3[S:31][CH:30]=[CH:29][CH:28]=3)=[O:33])[CH:11]=[CH:12][CH:13]=2)=[N:21]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 789282-Thiophenecarbonyl chlorideHCID 684582972-[6-(Aminomethyl)-2-pyridyl]-4h-1,3-benzothiazine-4-one trifluoroacetic acid salt

生成物 1

HCID 59750334N-[[6-(4-Oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]methyl]-2-thiophenecarboxamide収率 43.7%

試薬・触媒・溶媒 1

HCID 31374
Dimethylacetamide
溶媒

反応条件

温度
60 °C

実験手順

2-[6-(Aminomethyl)-2-pyridyl]-4H-1,3-benzothiazine-4-one trifluoroacetic acid salt (350 mg, 0.91 mmol) was dissolved in N,N-dimethylacetamide (10 ml), and 2-thenoyl chloride (400 mg, 2.72 mmol) was added thereto. The reaction mixture was stirred at 60° C. for 15 hrs and combined with ethyl acetate and water. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was subjected to a silica gel column chromatography. The fractions eluted with hexane-ethyl acetate (1:4, v/v) were collected, concentrated and recrystallized from hexane-tetrahydrofuran to give the titled compound (151 mg, 43%) as white crystals.

後処理

  1. washThe organic layer was washed with saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated
  4. washThe fractions eluted with hexane-ethyl acetate (1:4, v/v)
  5. customwere collected
  6. concentrationconcentrated
  7. customrecrystallized from hexane-tetrahydrofuran

出典と根拠

ORDレコード
ord-25fb1b2cb46148979a3b59bffd7e0920
出典データセット
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07767665B2

反応ノート

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