Phosphorus pentachloride → 4-(2-tert-butyl-4-nitro-1H-pyrrole-5-carbonyl)-3,3-dimethylpiperazin-2-one

HRID 18933

반응식

HRID 18933 반응식
[C:1]([C:5]1[NH:9][C:8]([C:10]([OH:12])=O)=[C:7]([N+:13]([O-:15])=[O:14])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].P(Cl)(Cl)(Cl)(Cl)Cl.[CH3:22][C:23]1([CH3:30])[NH:28][CH2:27][CH2:26][NH:25][C:24]1=[O:29].CCN(C(C)C)C(C)C>ClCCl>[C:1]([C:5]1[NH:9][C:8]([C:10]([N:28]2[CH2:27][CH2:26][NH:25][C:24](=[O:29])[C:23]2([CH3:30])[CH3:22])=[O:12])=[C:7]([N+:13]([O-:15])=[O:14])[CH:6]=1)([CH3:2])([CH3:3])[CH3:4]

참가 물질

6

반응물 4

HCID 24819Phosphorus pentachlorideHCID 81531DiisopropylethylamineHCID 2111572-Piperazinone, 3,3-dimethyl-HCID 183223915-tert-butyl-3-nitro-1H-pyrrole-2-carboxylic acid

생성물 1

HCID 586792724-(2-tert-butyl-4-nitro-1H-pyrrole-5-carbonyl)-3,3-dimethylpiperazin-2-one수율 53.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

The previously prepared 5-tert-butyl-3-nitro-1H-pyrrole-2-carboxylic acid (0.203 g, 1.11 mmol) and PCl5 (0.232 g, 1.11 mmol) were dissolved in dichloromethane (4 mL) and stirred at room temperature for 5 minutes. The resulting solution was added in one portion to a solution of 3,3-dimethylpiperazin-2-one (0.214 g, 1.67 mmol) and DIEA (0.288 g, 2.23 mmol) in dichloromethane (3 mL) and stirred at room temperature for 5 minutes. The reaction mixture was diluted with dichloromethane and washed sequentially with 1N aqueous HCl, saturated sodium bicarbonate, dried and the solvent removed under vacuum. The crude product was purified by chromatographic column (silica gel, dichloromethane:methanol, 95:5) to afford 0.190 g of expected 4-(2-tert-butyl-4-nitro-1H-pyrrole-5-carbonyl)-3,3-dimethylpiperazin-2-one.

후처리

  1. stirringstirred at room temperature for 5 minutes
  2. washwashed sequentially with 1N aqueous HCl, saturated sodium bicarbonate
  3. customdried
  4. customthe solvent removed under vacuum
  5. customThe crude product was purified by chromatographic column (silica gel, dichloromethane:methanol, 95:5)

출처 및 근거

ORD 기록
ord-322741f3750e433294754e2aba2b83fd
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741479B2

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