Potassium Carbonate → 3-(9-Chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)-piperidine-1-carboxylic acid benzylamide

HRID 2212198

反応式

HRID 2212198 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.[CH2:24]([N:31]=[C:32]=[O:33])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[CH2:24]([NH:31][C:32]([N:15]1[CH2:16][CH2:17][CH2:18][CH:13]([N:8]2[C:9]3[CH:10]=[CH:11][CH:12]=[C:3]([Cl:2])[C:4]=3[C:5]3=[N:22][O:21][C:20]([CH3:23])=[C:6]3[C:7]2=[O:19])[CH2:14]1)=[O:33])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 76639Benzyl isocyanateHCID 219637129-Chloro-3-methyl-5-piperidin-3-yl-5H-isoxazolo[4,3-c]quinolin-4-one hydroiodide

生成物 1

HCID 696524153-(9-Chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)-piperidine-1-carboxylic acid benzylamide収率 89.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a 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 tetrahydrofuran (3 mL) add benzyl isocyanate (16 μL, 0.12 mmol) and follow by potassium carbonate (23 mg, 0.17). Stir the mixture at room temperature under nitrogen overnight. concentrate the mixture, partition between 20% isopropanol/chloroform and water, and separate. Wash 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 44.4 mg of the title compound as an orange solid, 88% yield. 1H NMR: consistent with structure. MS (ion spray) 451 (M+).

後処理

  1. concentrationconcentrate the mixture
  2. custompartition between 20% isopropanol/chloroform and water
  3. customseparate
  4. washWash the organic layer with saturated aqueous sodium bicarbonate solution, brine
  5. dry with materialdry over magnesium sulfate
  6. concentrationconcentrate
  7. 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-184b0e13f5384e9db8be023ae7358daf
出典データセット
uspto-grants-2006_09
特許番号
US07101891B2

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