2,5-Dimethyl-1-phenylpyrrole-3-carboxaldehyde → Pyrvinium Pamaote Impurity 3

HRID 1642351노트

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HRID 1642351 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]2[CH:8]=[C:9]([N:12]([CH3:14])[CH3:13])[CH:10]=[CH:11][C:4]=2[N:3]=1.[CH3:15][C:16]1[N:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]([CH3:23])=[CH:19][C:20]=1[CH:21]=O>CN(C=O)C.[OH-].[Na+].[Cl-].[Cl-].[Zn+2]>[CH3:14][N:12]([CH3:13])[C:9]1[CH:8]=[C:5]2[C:4](=[CH:11][CH:10]=1)[N:3]=[C:2](/[CH:1]=[CH:21]/[C:20]1[CH:19]=[C:18]([CH3:23])[N:17]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:16]=1[CH3:15])[CH:7]=[CH:6]2

참가 물질

6

반응물 2

HCID 665152,5-Dimethyl-1-phenylpyrrole-3-carboxaldehydeHCID 667256-Quinolinamine, N,N,2-trimethyl-

생성물 1

HCID 25015775Pyrvinium Pamaote Impurity 3수율 2.1%

시약·촉매·용매 3

HCID 3007855Zincchloride촉매HCID 6228Dimethylformamide용매HCID 14798Sodium Hydroxide용매

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온도
160 °C

실험 절차

To a solution of compound 3 (316 mg, 1.7 mmol) and compound 5 (507 mg, 2.55 mmol) in DMF (25 mL) was added ZnCl2 (232 mg, 1.7 mmol). The reaction mixture was stirred at 160° C. overnight. Then the reaction mixture was diluted with aqueous NaOH (10%) and extracted with EtOAc. The organic layer was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure, the residue was purified by column chromatography (hexane:EtOAc=20:1) to give 13 mg of the target product (2.1%). MS[M++1]=368, LC-MS: tR=1.909 min

후처리

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4
  3. customthe solvent was removed under reduced pressure
  4. customthe residue was purified by column chromatography (hexane:EtOAc=20:1)

출처 및 근거

ORD 기록
ord-5d24bac05cac4800a7e07b766a4fb763
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08119660B2

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