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 856365ノート

反応式

HRID 856365 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-73392b5fc78545599fb5fb94d4dfe5c8
出典データセット
uspto-grants-2007_08
特許番号
US07262212B2

反応ノート

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