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

HRID 2212198

반응식

HRID 2212198 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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+).

후처리

  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)

출처 및 근거

ORD 기록
ord-184b0e13f5384e9db8be023ae7358daf
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07101891B2

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