Potassium Carbonate → 1,3-dimethyl-5-(4-methylpiperazin-1-yl)-1H-pyrazole-4-carbaldehyde

HRID 859748ノート

反応式

HRID 859748 の反応式
Cl[C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH3:8])[C:3]=1[CH:9]=[O:10].[CH3:11][N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+]>CN(P(N(C)C)(N(C)C)=O)C.O>[CH3:7][N:6]1[C:2]([N:15]2[CH2:16][CH2:17][N:12]([CH3:11])[CH2:13][CH2:14]2)=[C:3]([CH:9]=[O:10])[C:4]([CH3:8])=[N:5]1

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 531671-MethylpiperazineHCID 27773975-Chloro-1,3-dimethylpyrazole-4-carboxaldehyde

生成物 1

HCID 337871101,3-dimethyl-5-(4-methylpiperazin-1-yl)-1H-pyrazole-4-carbaldehyde収率 29%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 12679Hexamethylphosphoramide溶媒

実験手順

To a solution of 5-chloro-1,3-dimethyl-1H-pyrazole-4-carbaldehyde (25.4 g, 0.16 mol) in HMPA (25 mL) and water (25 mL) was added 1-methylpiperazine (40 g, 0.4 mol, 2.5 equiv), and the mixture was heated at 120–125° C. for 25 h. When the reaction was completed, the reaction mixture was poured into water (500 mL), and potassium carbonate was added to make the medium strongly alkaline. The mixture was extracted with dichloromethane (5×100 mL). The combined organic extracts were washed twice with water and dried with sodium sulfate, and the solvent evaporated. The residue was purified chromatographically on silica gel with gradient elution from dichloromethane to methanol, affording 10.2 g (29%) of the title product. Satisfactory C,H,N-analysis was obtained. 1H NMR (400 MHz, DMSO-d6): δ 2.23 (s, 3H), 2.26 (s, 3H), 2.44 (m, 4H), 3.16 (m, 4H), 3.59 (s, 3H), 9.88 (s, 1H). LC-MS (API-ES) calcd for C11H18N4O: 222.15, found (M+H+): 223.1 m/z.

後処理

  1. temperaturethe mixture was heated at 120–125° C. for 25 h
  2. additionwas added
  3. extractionThe mixture was extracted with dichloromethane (5×100 mL)
  4. washThe combined organic extracts were washed twice with water
  5. dry with materialdried with sodium sulfate
  6. customthe solvent evaporated
  7. customThe residue was purified chromatographically on silica gel with gradient elution from dichloromethane to methanol

出典と根拠

ORDレコード
ord-3631a6646e4f4892a145953696fd8fe7
出典データセット
uspto-grants-2006_12
特許番号
US07151105B2

反応ノート

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