Triethylamine → (3,4-Diaminophenyl)(4-methylpiperazin-1-yl)methanone

HRID 21119

反応式

HRID 21119 の反応式
C1C=C2N=NN(O)C2=CC=1.O.C(N(CC)CC)C.C(OC(Cl)=O)C.[NH2:25][C:26]1[CH:27]=[C:28]([CH:32]=[CH:33][C:34]=1[NH2:35])[C:29]([OH:31])=O.[CH3:36][N:37]1[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1>CN(C=O)C.O>[NH2:25][C:26]1[CH:27]=[C:28]([C:29]([N:40]2[CH2:41][CH2:42][N:37]([CH3:36])[CH2:38][CH2:39]2)=[O:31])[CH:32]=[CH:33][C:34]=1[NH2:35]

参加物

8

反応物 5

HCID 8471Triethylamine2 回HCID 10928Ethyl chloroformateHCID 531671-MethylpiperazineHCID 692633,4-Diaminobenzoic acidHCID 27960291-Hydroxybenzotriazole hydrate

生成物 1

HCID 29919691(3,4-Diaminophenyl)(4-methylpiperazin-1-yl)methanone収率 18%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
0 °C

実験手順

HOBT monohydrate (2.00 g, 13.1 mmol) was dissolved in DMF (20 mL), and the solution was added with triethylamine (2.54 mL, 18.2 mmol) and ethylchloroformate (1.24 mL, 13.0 mmol), followed by stirring at 0° C. for 3 hours. Then, the mixture was added with triethylamine (4.22 mL, 30.3 mmol) and 3,4-diaminobenzoic acid (1.86 g, 12.2 mmol), followed by stirring at the same temperature for 2 hours. The mixture was added with a solution of N-methylpiperazine (1.21 mL, 10.9 mmol) in DMF (20 mL), followed by further stirring for 30 minutes. The reaction mixture was added with water (2 mL) and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol/7 mol/L ammonia-methanol solution=50/0.5/0.5-7/0.5/0.5) and preparative thin-layer chromatography (chloroform/methanol/7 mol/L ammonia-methanol solution=4/0.5/0.5) to obtain (3,4-diaminophenyl)(4-methylpiperazin-1-yl)methanone (455 mg, yield 18%).

後処理

  1. stirringby stirring at the same temperature for 2 hours
  2. stirringby further stirring for 30 minutes
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (chloroform/methanol/7 mol/L ammonia-methanol solution=50/0.5/0.5-7/0.5/0.5)

出典と根拠

ORDレコード
ord-7c9f628c125a4b0fa7dd23f26f63f52c
出典データセット
uspto-grants-2010_06
特許番号
US07745641B2

関連ノート

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