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Methyl iodide → HCID 67215732, 화합물

HRID 1677566
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HRID 1677566 반응식
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[CH:11][C:12]2[N:13]([C:15]([C:18]([C:20]3[CH:21]=[CH:22][C:23]([N+:30]([O-:32])=[O:31])=[C:24]([CH:29]=3)[C:25]([O:27][CH3:28])=[O:26])=[O:19])=[N:16][CH:17]=2)[CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:35]I.S([O-])(O)(=O)=O.[K+]>CN(C)C=O>[C:1]([O:5][C:6]([N:8]([CH3:35])[C:9]1[CH:10]=[CH:11][C:12]2[N:13]([C:15]([C:18]([C:20]3[CH:21]=[CH:22][C:23]([N+:30]([O-:32])=[O:31])=[C:24]([CH:29]=3)[C:25]([O:27][CH3:28])=[O:26])=[O:19])=[N:16][CH:17]=2)[CH:14]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 516920Potassium bisulfateHCID 67215620HCID 67215620, 화합물

생성물 1

HCID 67215732HCID 67215732, 화합물수율 85%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

540 mg (1.23 mmol) of methyl 5-({6-[(tertbutoxycarbonyl)amino]imidazo[1,5-a]pyridin-3-yl}carbonyl)-2-nitrobenzoate in 10 ml of dimethylformamide are added to 53.9 mg (1.35 mmol) of sodium hydride (60% dispersion in oil) in 2 ml of dimethylformamide, the mixture is stirred at ambient temperature for 30 minutes, then 84 μl (1.35 mmol) of methyl iodide are added and the mixture is left stirring at ambient temperature overnight. The mixture is acidified to pH=4 with an aqueous potassium hydrogensulfate solution and extracted with ethyl acetate. The organic phase is washed with a saturated aqueous sodium chloride solution, then dried over sodium sulfate and concentrated under reduced pressure. The product is purified by filtration through a bed of silica, elution being carried out with dichloromethane. 475 mg of an orange-colored powder are obtained. Melting point: 55° C.; 1H NMR (d6-DMSO): 1.46 (9H, s), 3.33 (3H, s), 3.92 (3H, s), 7.57 (1H, d), 7.98 (1H, s), 8.06 (1H, d), 8.25 (1H, d), 8.68 (1H, d), 8.76 (1H, s), 9.77 (1H, s)

후처리

  1. waitthe mixture is left
  2. stirringstirring at ambient temperature overnight
  3. extractionextracted with ethyl acetate
  4. washThe organic phase is washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. filtrationThe product is purified by filtration through a bed of silica, elution

출처 및 근거

ORD 기록
ord-ddefd11d531b4f2db5f94807767a9b48
출처 데이터셋
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08008321B2

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