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

HRID 641810

反応式

HRID 641810 の反応式
[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

参加物

6

反応物 2

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

生成物 1

HCID 25015775Pyrvinium Pamaote Impurity 3収率 2.1%

試薬・触媒・溶媒 3

HCID 3007855Zincchloride触媒HCID 6228Dimethylformamide溶媒HCID 14798Sodium Hydroxide溶媒

反応条件

温度
160 °C

実験手順

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

後処理

  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)

出典と根拠

ORDレコード
ord-542751499db846c49ec3256d8634c523
出典データセット
uspto-grants-2010_04
特許番号
US07696227B2

関連ノート

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