Triphenylphosphine → 4-Chloro-3-(4-methyl-2-oxo-1-piperazinyl)-5-nitrobenzonitrile

HRID 921867ノート

反応式

HRID 921867 の反応式
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.[Cl:34][C:35]1[C:40]([N+:41]([O-:43])=[O:42])=[CH:39][C:38]([C:44]#[N:45])=[CH:37][C:36]=1[NH:46][C:47](=O)[CH2:48][N:49]([CH2:51][CH2:52][OH:53])[CH3:50]>C1COCC1.CCOC(C)=O.O>[Cl:34][C:35]1[C:40]([N+:41]([O-:43])=[O:42])=[CH:39][C:38]([C:44]#[N:45])=[CH:37][C:36]=1[N:46]1[CH2:47][CH2:48][N:49]([CH3:50])[CH2:51][C:52]1=[O:53]

参加物

7

反応物 3

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 89923330HCID 89923330、化合物

生成物 1

HCID 899234104-Chloro-3-(4-methyl-2-oxo-1-piperazinyl)-5-nitrobenzonitrile収率 35.3%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of triphenylphosphine (252 mg, 0.959 mmol) in THF (2 mL) was added DIAD (0.187 mL, 0.959 mmol). The reaction mixture was stirred for 10 min. Then a solution of N-(2-chloro-5-cyano-3-nitrophenyl)-2-((2-hydroxyethyl)(methyl)amino)acetamide (120 mg, 0.384 mmol) in THF (2 mL) was added drop wise. The reaction mixture was then stirred at room temperature for 2 h. LC-MS indicated the desired peak, but the reaction was about ˜80% complete. It was diluted with EtOAc and water. The aqueous layer was extracted with EtOAc and the combined organic layer was washed with water, brine, dried over Na2SO4, filtered and concentrated. Purification via silica gel chromatography (0-100% EtOAc in Hexanes, 12 g) gave 4-chloro-3-(4-methyl-2-oxopiperazin-1-yl)-5-nitrobenzonitrile (40 mg) as a off-white solid.

後処理

  1. stirringThe reaction mixture was then stirred at room temperature for 2 h
  2. extractionThe aqueous layer was extracted with EtOAc
  3. washthe combined organic layer was washed with water, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification via silica gel chromatography (0-100% EtOAc in Hexanes, 12 g)

出典と根拠

ORDレコード
ord-e0c7873ec59c46e7b6b81792a4cb7541
出典データセット
uspto-grants-2016_03
特許番号
US09273057B2

反応ノート

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