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

HRID 459868
ノート
印刷プレビュー

反応式

HRID 459868 の反応式
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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962
Water
溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-1c01d216e0cd42eabb9a1cc79af91373
出典データセット
uspto-grants-2007_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07196080B2

反応ノート

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