Water → HCID 67480855、化合物

HRID 1295726ノート

反応式

HRID 1295726 の反応式
Cl[C:2]1[C:3]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:10]([CH3:21])[CH2:9]2)=[N:4][CH:5]=[CH:6][N:7]=1.C[C:23]([O-:26])([CH3:25])C.[K+].[OH2:28]>C(O)CO.O1CCOCC1>[C:17]([O:16][C:14]([N:11]1[CH2:12][CH2:13][N:8]([C:3]2[C:2]([O:28][CH2:25][CH2:23][OH:26])=[N:7][CH:6]=[CH:5][N:4]=2)[CH2:9][CH:10]1[CH3:21])=[O:15])([CH3:20])([CH3:19])[CH3:18]

参加物

6

反応物 3

HCID 962WaterHCID 23665647Potassium tert-butoxideHCID 86760515HCID 86760515、化合物

生成物 1

HCID 67480855HCID 67480855、化合物収率 98%

試薬・触媒・溶媒 2

HCID 174Ethylene Glycol溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
90 °C

実験手順

To a mixture of tert-butyl 4-(3-chloropyrazin-2-yl)-2-methylpiperazine-1-carboxylate (3.0 g, 9.6 mmol; from Step 2) in ethylene glycol (10 mL) and dioxane (30 mL) was added t-BuOK (1.18 g, 10.6 mmol). The resulting mixture was stirred at 90° C., under N2, overnight. Water (10 mL) was added to the light brown reaction mixture and extracted with dichloromethane (3×20 mL). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by column chromatography using toluene/EtOAc (2:3) as eluent to furnish 3.19 g (98%) of the title compound. HPLC purity: 99%. MS m/z 339 (M+H)+. HRMS m/z calcd for C16H26N4O4(M)+ 338.1954, found 338.1953.

後処理

  1. extractionextracted with dichloromethane (3×20 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography

出典と根拠

ORDレコード
ord-9b047ae8a5294ab98eb48cc7eadcfbce
出典データセット
uspto-grants-2007_07
特許番号
US07244722B2

反応ノート

読み込み中…