Phenylmethanesulfonyl chloride → 9-Chloro-3-methyl-5-(1-phenylmethanesulfonyl-piperidin-3-yl)-5H-isoxazolo[4,3-c]quinolin-4-one

HRID 2212199

反応式

HRID 2212199 の反応式
I.[Cl:2][C:3]1[C:4]2[C:5]3[C:6](=[C:20]([CH3:23])[O:21][N:22]=3)[C:7](=[O:19])[N:8]([CH:13]3[CH2:18][CH2:17][CH2:16][NH:15][CH2:14]3)[C:9]=2[CH:10]=[CH:11][CH:12]=1.N12CCCN=C1CCCCC2.[C:35]1([CH2:41][S:42](Cl)(=[O:44])=[O:43])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>C(O)C>[Cl:2][C:3]1[C:4]2[C:5]3[C:6](=[C:20]([CH3:23])[O:21][N:22]=3)[C:7](=[O:19])[N:8]([CH:13]3[CH2:18][CH2:17][CH2:16][N:15]([S:42]([CH2:41][C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)(=[O:44])=[O:43])[CH2:14]3)[C:9]=2[CH:10]=[CH:11][CH:12]=1

参加物

5

反応物 3

HCID 74740Phenylmethanesulfonyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 219637129-Chloro-3-methyl-5-piperidin-3-yl-5H-isoxazolo[4,3-c]quinolin-4-one hydroiodide

生成物 1

HCID 219637239-Chloro-3-methyl-5-(1-phenylmethanesulfonyl-piperidin-3-yl)-5H-isoxazolo[4,3-c]quinolin-4-one収率 73%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a 0° C. suspension of 9-chloro-3-methyl-5-piperidin-3-yl-5H-isoxazolo[4,3-c]quinolin-4-one hydroiodide (50 mg, 0.11 mmol) in ethanol (5 mL) add 1,8-diazabicyclo[5.4.0]undec-7-ene (42 μL, 0.28 mmol). Stir the solution for 10 mins. To the solution add α-toluene-sulfonyl chloride (21 mg, 0.11 mmol) and stir the reaction at 0° C. under nitrogen for 30 minutes. Quench the reaction with 1N HCl, concentrate, and extract with 20% isopropanol/chloroform (×2). Wash the combined organic layers with saturated aqueous sodium bicarbonate solution, brine, dry over magnesium sulfate and concentrate. Purify by flash chromatography on silica gel (eluting with 0–0.4% methanol/chloroform) to give 37.9 mg of the title compound as a white solid, 72% yield. 1H NMR: consistent with structure. MS (ion spray) 472 (M+).

後処理

  1. stirringstir
  2. customthe reaction at 0° C. under nitrogen for 30 minutes
  3. customQuench
  4. customthe reaction with 1N HCl
  5. concentrationconcentrate
  6. extractionextract with 20% isopropanol/chloroform (×2)
  7. washWash the combined organic layers with saturated aqueous sodium bicarbonate solution, brine
  8. dry with materialdry over magnesium sulfate
  9. concentrationconcentrate
  10. customPurify by flash chromatography on silica gel (eluting with 0–0.4% methanol/chloroform)

出典と根拠

ORDレコード
ord-606f274b3ba447d89bb53890261a59cd
出典データセット
uspto-grants-2006_09
特許番号
US07101891B2

関連ノート

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