Potassium Iodide → 2-[3-(9-chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)-piperidin-1-yl]-N-(3,4,5-trimethoxy-phenyl)-acetamide

HRID 2212197

反応式

HRID 2212197 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.Br[CH2:25][C:26]([NH:28][C:29]1[CH:34]=[C:33]([O:35][CH3:36])[C:32]([O:37][CH3:38])=[C:31]([O:39][CH3:40])[CH:30]=1)=[O:27].[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[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]([CH2:25][C:26]([NH:28][C:29]4[CH:30]=[C:31]([O:39][CH3:40])[C:32]([O:37][CH3:38])=[C:33]([O:35][CH3:36])[CH:34]=4)=[O:27])[CH2:14]3)[C:9]=2[CH:10]=[CH:11][CH:12]=1

参加物

6

反応物 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 219637112-Bromo-N-(3,4,5-trimethoxy-phenyl)-acetamideHCID 219637129-Chloro-3-methyl-5-piperidin-3-yl-5H-isoxazolo[4,3-c]quinolin-4-one hydroiodide

生成物 1

HCID 219637142-[3-(9-chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)-piperidin-1-yl]-N-(3,4,5-trimethoxy-phenyl)-acetamide収率 63.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Add 9-chloro-3-methyl-5-piperidin-3-yl-5H-isoxazolo[4,3-c]quinolin-4-one hydroiodide (50 mg, 0.11 mmol), 2-bromo-N-(3,4,5-trimethoxy-phenyl)-acetamide (38 mg, 0.12 mmol), and tetrahydrofuran (3 mL) to a roundbottom flask. Stir and add potassium iodide (2 mg, 0.01 mmol) and potassium carbonate (34 mg, 0.25 mmol) at room temperature under nitrogen overnight. Concentrate the reaction, partitions between water and 20% isopropanol/chloroform, and separate. Was the organic layer with saturated aqueous sodium bicarbonate solution, brine, dry over magnesium sulfate and concentrate. Purify by flash chromatography on silica gel (eluting with 0–0.5% methanol/chloroform) to give 37.6 mg of the title compound as an orange solid, 62% yield. 1H NMR: consistent with structure. MS (ion spray) 541 (M+).

後処理

  1. concentrationConcentrate
  2. customthe reaction, partitions between water and 20% isopropanol/chloroform
  3. customseparate
  4. dry with materialdry over magnesium sulfate
  5. concentrationconcentrate
  6. customPurify by flash chromatography on silica gel (eluting with 0–0.5% methanol/chloroform)

出典と根拠

ORDレコード
ord-fbbecfc0e325409da1c44840f8581115
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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