Potassium Iodide → 1-Tert-butyl-4-[2-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-yl)ethyl]piperazin-2-one

HRID 856365노트

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HRID 856365 반응식
CS(O[CH2:6][CH2:7][C:8]1([CH3:19])[O:12][C:11]2=[N:13][C:14]([N+:16]([O-:18])=[O:17])=[CH:15][N:10]2[CH2:9]1)(=O)=O.Cl.[C:21]([N:25]1[CH2:30][CH2:29][NH:28][CH2:27][C:26]1=[O:31])([CH3:24])([CH3:23])[CH3:22].C(N(CC)CC)C.[I-].[K+]>O.CN(C=O)C>[C:21]([N:25]1[CH2:30][CH2:29][N:28]([CH2:6][CH2:7][C:8]2([CH3:19])[O:12][C:11]3=[N:13][C:14]([N+:16]([O-:18])=[O:17])=[CH:15][N:10]3[CH2:9]2)[CH2:27][C:26]1=[O:31])([CH3:24])([CH3:22])[CH3:23]

참가 물질

7

반응물 4

HCID 4875Potassium IodideHCID 8471TriethylamineHCID 230810922-(2-Methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-yl)ethyl methanesulfonateHCID 23081273HCID 23081273, 화합물

생성물 1

HCID 230812141-Tert-butyl-4-[2-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-yl)ethyl]piperazin-2-one수율 8%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
70 °C

실험 절차

A mixture of 2-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-yl)ethyl methanesulfonate prepared in Example 42 (290 mg, 1 mmol), 1-tert-butylpiperazin-2-one hydrochloride (200 mg, 1.28 mmol), triethylamine (242 mg, 2.39 mmol), potassium iodide (250 mg, 1.5 mmol) and DMF (3 ml) was stirred at 70° C. for 4 hours. The reaction mixture was allowed to return to room temperature. To the solution, water was added, and the resulting solution was extracted with ethyl acetate twice. The organic phases were combined, washed with water twice and a saturated saline solution, dried over magnesium sulfate and then filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (methylene chloride/methanol=20/1) to afford 1-tert-butyl-4-[2-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-yl)ethyl]piperazin-2-one (27 mg, yield 8%) as a white powder.

후처리

  1. customto return to room temperature
  2. extractionthe resulting solution was extracted with ethyl acetate twice
  3. washwashed with water twice
  4. dry with materiala saturated saline solution, dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (methylene chloride/methanol=20/1)

출처 및 근거

ORD 기록
ord-73392b5fc78545599fb5fb94d4dfe5c8
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07262212B2

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