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

HRID 18936

反応式

HRID 18936 の反応式
[C:1]([C:5]1[NH:9][C:8]([N+:10]([O-:12])=[O:11])=[C:7]([C:13]([OH:15])=O)[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].C(NCC)C.C([O-])(O)=O.[Na+]>C1C=CC=CC=1.ClCCl>[C:1]([C:5]1[NH:9][C:8]([N+:10]([O-:12])=[O:11])=[C:7]([C:13]([N:28]2[CH2:27][CH2:26][NH:25][C:24](=[O:29])[C:23]2([CH3:30])[CH3:22])=[O:15])[CH:6]=1)([CH3:2])([CH3:3])[CH3:4]

参加物

8

反応物 5

HCID 8021DiethylamineHCID 24819Phosphorus pentachloride2 回HCID 2111572-Piperazinone, 3,3-dimethyl-HCID 516892Sodium BicarbonateHCID 586792985-tert-butyl-2-nitro-1H-pyrrole-3-carboxylic acid

生成物 1

HCID 586793674-(2-tert-butyl-5-nitro-1H-pyrrole-4-carbonyl)-3,3-dimethylpiperazin-2-one収率 49%

試薬・触媒・溶媒 2

HCID 241Benzene溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

To 5-tert-butyl-2-nitro-1H-pyrrole-3-carboxylic acid (100 mg, 0.47 mmol) in benzene (2 mL) was added solid PCl5 (120 mg, 0.57 mmol). The resulting reaction mixture was stirred at RT until all the PCl5 went into the solution. This reaction mixture was then added to 3,3-dimethylpiperazin-2-one (120 mg, 0.94 mmol) and diethylamine (280 ml, 0.94 mmol) in dichloromethane (DCM) (3 mL). After 30 min, the reaction was diluted with DCM (10 mL) and followed by addition of sat. NaHCO3. The organic phase was then washed with 1N HCl and brine, dried, and concentrated in vacuo. This crude product was further purified using flash chromatography (EtOAc/Hexane: 1/4) to provide 4-(2-tert-butyl-5-nitro-1H-pyrrole-4-carbonyl)-3,3-dimethylpiperazin-2-one 6 (74 mg, 49%) as yellow foam.

後処理

  1. customThe resulting reaction mixture
  2. washThe organic phase was then washed with 1N HCl and brine
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThis crude product was further purified

出典と根拠

ORDレコード
ord-f5ad1f4198a44773b190983f0e144bdc
出典データセット
uspto-grants-2010_06
特許番号
US07741479B2

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