3-Chlorobenzenesulphonyl chloride → 3-Chloro-N-{2-methyl-6-(methyloxy)-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-yl}benzenesulfonamide

HRID 573688ノート

反応式

HRID 573688 の反応式
[CH3:1][C:2]1[S:13][C:5]2[N:6]=[C:7]([O:11][CH3:12])[CH:8]=[C:9]([NH2:10])[C:4]=2[C:3]=1[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[Cl:32][C:33]1[CH:34]=[C:35]([S:39](Cl)(=[O:41])=[O:40])[CH:36]=[CH:37][CH:38]=1>C1COCC1>[Cl:32][C:33]1[CH:34]=[C:35]([S:39]([NH:10][C:9]2[CH:8]=[C:7]([O:11][CH3:12])[N:6]=[C:5]3[S:13][C:2]([CH3:1])=[C:3]([C:14]4[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=4)[C:4]=23)(=[O:41])=[O:40])[CH:36]=[CH:37][CH:38]=1

参加物

5

反応物 3

HCID 179093-Chlorobenzenesulphonyl chlorideHCID 2733832Lithium HexamethyldisilazideHCID 683241312-Methyl-6-(methyloxy)-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-amine

生成物 1

HCID 683237633-Chloro-N-{2-methyl-6-(methyloxy)-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-yl}benzenesulfonamide収率 42.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 2-methyl-6-(methyloxy)-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-amine (Description 37) (16.5 mg, 0.055 mmol) in THF (0.5 mL) at −78° C. under a nitrogen atmosphere was added LiHMDS (1M solution in THF) (0.055 mL, 0.055 mmol). The solution was stirred at −78° C. for ca. 10 min before the addition of 3-chlorobenzenesulfonyl chloride (7.73 μL, 0.055 mmol). The reaction mixture was then warmed to RT under a nitrogen atmosphere overnight and was then partitioned between water and ethyl acetate (ca. 10 mL each). The aqueous layer was separated and re-extracted with ethyl acetate (ca. 10 mL). The combined organic layer was passed through phase separator and the solvent concentrated in vacuo. The residue was purified by MDAP (acidic conditions), to give the title compound (11 mg). LCMS (A) m/z: 475 [M+1]+, Rt 1.63 min (acidic).

後処理

  1. customwas then partitioned between water and ethyl acetate (ca. 10 mL each)
  2. customThe aqueous layer was separated
  3. extractionre-extracted with ethyl acetate (ca. 10 mL)
  4. concentrationthe solvent concentrated in vacuo
  5. customThe residue was purified by MDAP (acidic conditions)

出典と根拠

ORDレコード
ord-349f63cb3f2746fd804b2b70ef5dda9a
出典データセット
uspto-grants-2015_05
特許番号
US09029545B2

反応ノート

読み込み中…