تفاعل #2439959

ord-595e417efb4e4157a8963a91b7e80c40

معادلة التفاعل

CCn1nc(C)cc1C(=O)Nc1ccc(Cc2ccc3c(c2)C(=CO)C(=O)N3)cc1
2-Ethyl-5-methyl-2H-pyrazole-3-carboxylic acid [4-(3-hydroxymethylene-2-oxo-2,3-dihydro-1H-indol-5-ylmethyl)-phenyl]-amide
C1CCOC1
THF
CN1CCN(c2ccc(N)cc2)CC1
4-(4-Methyl-piperazin-1-yl)-phenylamine
CCn1nc(C)cc1C(=O)Nc1ccc(Cc2ccc3c(c2)C(=CNc2ccc(N4CCN(C)CC4)cc2)C(=O)N3)cc1
desired product
المردود 55.0%
CCn1nc(C)cc1C(=O)Nc1ccc(Cc2ccc3c(c2)C(=CNc2ccc(N4CCN(C)CC4)cc2)C(=O)N3)cc1
2-Ethyl-5-methyl-2H-pyrazole-3-carboxylic acid [4-(3-{[4-(4-methyl-piperazin-1-yl)-phenylamino]-methylene}-2-oxo-2,3-dihydro-1H-indol-5-ylmethyl)-phenyl]-amide
المردود 55.0%

المذيبات

ظروف التفاعل

درجة الحرارة
65°CELSIUS
الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىA small screw cap test tube
  2. 2
    درجة الحرارةSubsequently, the reaction mixture was cooled to room temperature
  3. 3
    غسيلThe solution was washed with water (2 mL)
  4. 4
    غسيلthe water layer was re-washed with additional EtOAc (2 mL)
  5. 5
    تركيزThe combined organic layers were then concentrated in vacuo
  6. 6
    أخرىaffording the crude product
  7. 7
    أخرىThe crude product was further purified by silica gel column chromatography with 5% methanol in chloroform as eluant

الإجراء التجريبي

A small screw cap test tube was charged with 2-Ethyl-5-methyl-2H-pyrazole-3-carboxylic acid [4-(3-hydroxymethylene-2-oxo-2,3-dihydro-1H-indol-5-ylmethyl)-phenyl]-amide (prepared below, 70 mg, 0.175 mmol) and THF (1 mL). To the resulting solution was added 4-(4-Methyl-piperazin-1-yl)-phenylamine (66.8 mg, 0.349 mmol), and the mixture was stirred for 24 h at 65° C. Subsequently, the reaction mixture was cooled to room temperature and then diluted with EtOAc (2 mL). The solution was washed with water (2 mL) and the water layer was re-washed with additional EtOAc (2 mL). The combined organic layers were then concentrated in vacuo affording the crude product. The crude product was further purified by silica gel column chromatography with 5% methanol in chloroform as eluant to give the desired product as a solid in 55% yield (55 mg, 0.96 mmol).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US07749530B2uspto-grants-2010_07