Potassium bis(trimethylsilyl)amide → 3-(9-chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)-piperidine-1-carboxylic acid methyl ester

HRID 2212191

반응식

HRID 2212191 반응식
C[Si]([N-][Si](C)(C)C)(C)C.[K+].[CH3:11][O:12][C:13]([N:15]1[CH2:20][CH2:19][CH2:18][CH:17]([NH:21][C:22]([C:24]2[C:25]([C:30]3[C:35](F)=[CH:34][CH:33]=[CH:32][C:31]=3[Cl:37])=[N:26][O:27][C:28]=2[CH3:29])=[O:23])[CH2:16]1)=[O:14]>CN(C)C=O>[CH3:11][O:12][C:13]([N:15]1[CH2:20][CH2:19][CH2:18][CH:17]([N:21]2[C:35]3[CH:34]=[CH:33][CH:32]=[C:31]([Cl:37])[C:30]=3[C:25]3=[N:26][O:27][C:28]([CH3:29])=[C:24]3[C:22]2=[O:23])[CH2:16]1)=[O:14]

참가 물질

4

반응물 2

HCID 3251421Potassium bis(trimethylsilyl)amideHCID 69652389HCID 69652389, 화합물

생성물 1

HCID 99515613-(9-chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)-piperidine-1-carboxylic acid methyl ester수율 92.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Add potassium bis(trimethylsilyl)-amide (5.5 mL, 2.73 mmol, 0.5 M in toluene) to a solution of 3-{[3-(2-chloro-6-fluoro-phenyl)-5-methyl-isoxazole-4-carbonyl]-amino}-piperidine-1-carboxylic acid methyl ester (0.72 g, 1.82 mmol) in dimethylformamide (56 mL). After 5 minutes, quench the reaction with 1N HCl and concentrate. Partition the resulting material between 20% isopropanol/chloroform and 1N HCl. Wash the organic layer with saturated aqueous sodium bicarbonate solution and brine, dry over magnesium sulfate, and concentrate. Purify by flash chromatography on silica gel (eluting with 0–0.5% methanol/chloroform) to give 632 mg of the title compound as a white solid, 92% yield. 1H NMR: consistent with structure. MS (ion spray) 376 (M+).

후처리

  1. customquench
  2. customthe reaction with 1N HCl
  3. concentrationconcentrate
  4. customPartition the resulting material between 20% isopropanol/chloroform and 1N HCl
  5. washWash the organic layer with saturated aqueous sodium bicarbonate solution and brine
  6. dry with materialdry over magnesium sulfate
  7. concentrationconcentrate
  8. customPurify by flash chromatography on silica gel (eluting with 0–0.5% methanol/chloroform)

출처 및 근거

ORD 기록
ord-98d59a58ccf449549ce5dfcde00cd7cb
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07101891B2

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