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

HRID 21119

반응식

HRID 21119 반응식
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]

참가 물질

8

반응물 5

HCID 8471Triethylamine2회HCID 10928Ethyl chloroformateHCID 531671-MethylpiperazineHCID 692633,4-Diaminobenzoic acidHCID 27960291-Hydroxybenzotriazole hydrate

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매2회

반응 조건

온도
0 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-7c9f628c125a4b0fa7dd23f26f63f52c
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745641B2

연결된 노트

불러오는 중…