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Potassium Carbonate → Tert-butyl 4-(5-chloropyrazin-2-YL)piperazine-1-carboxylate

HRID 459868
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HRID 459868 반응식
CN1C(=O)CCC1.Cl[C:9]1[CH:14]=[N:13][C:12]([Cl:15])=[CH:11][N:10]=1.[C:16]([O:20][C:21]([N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)=[O:22])([CH3:19])([CH3:18])[CH3:17].C(=O)([O-])[O-].[K+].[K+]>O>[Cl:15][C:12]1[CH:11]=[N:10][C:9]([N:26]2[CH2:25][CH2:24][N:23]([C:21]([O:20][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:22])[CH2:28][CH2:27]2)=[CH:14][N:13]=1
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참가 물질

6

반응물 4

HCID 11430Potassium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 143452tert-Butyl piperazine-1-carboxylateHCID 3362242,5-Dichloropyrazine

생성물 1

HCID 22931015Tert-butyl 4-(5-chloropyrazin-2-YL)piperazine-1-carboxylate수율 90.2%

시약·촉매·용매 1

HCID 962
Water
용매

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온도
100 °C

실험 절차

To an NMP (7.5 ml) solution of 1.51 g of 2,5-dichloropyrazine were added 2.00 g of 1-(t-butoxycarbonyl)piperazine and 2.00 g of potassium carbonate, followed by 1 hour of stirring under heating at 100° C. The mixture was cooled to room temperature, and water was added thereto, followed by extraction with ethyl acetate. The organic layer was washed with water and brine and then dried over anhydrous magnesium sulfate, and thereafter, the solvent was evaporated. The residue was purified by silica gel column chromatography (chloroform-methanol) to obtain 2.73 g of 2-chloro-5-(4-t-butoxycarbonylpiperazin-1-yl)pyrazine. Using this compound, 2-chloro-5-{4-[6-(3,4-dimethoxyphenyl)pyridine-2-carbonyl]piperazin-1-yl}pyrazine was obtained in a similar manner to Example 14 as colorless crystals.

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated
  6. customThe residue was purified by silica gel column chromatography (chloroform-methanol)

출처 및 근거

ORD 기록
ord-1c01d216e0cd42eabb9a1cc79af91373
출처 데이터셋
uspto-grants-2007_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07196080B2

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