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

HRID 921867노트

반응식

HRID 921867 반응식
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]

참가 물질

7

반응물 3

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 89923330HCID 89923330, 화합물

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-e0c7873ec59c46e7b6b81792a4cb7541
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09273057B2

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