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4-(Chloromethyl)benzoyl chloride → [4-(Chloromethyl)phenyl]-n-[5-(4-(3-pyridyl)pyrimidin-2-yloxy)benzimidazol-2-yl]carboxamide

HRID 1790686
ノート
印刷プレビュー

反応式

HRID 1790686 の反応式
[S-][C:2]#[N:3].[Na+].[Cl:5][CH2:6][C:7]1[CH:15]=[CH:14][C:10]([C:11](Cl)=[O:12])=[CH:9][CH:8]=1.[N:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]2[CH:27]=[CH:26][N:25]=[C:24]([O:28][C:29]3[CH:30]=[C:31]([NH2:36])[C:32]([NH2:35])=[CH:33][CH:34]=3)[N:23]=2)[CH:17]=1.Cl.C(N=C=NCCCN(C)C)C>CC(C)=O>[Cl:5][CH2:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([NH:3][C:2]2[NH:36][C:31]3[CH:30]=[C:29]([O:28][C:24]4[N:23]=[C:22]([C:18]5[CH:17]=[N:16][CH:21]=[CH:20][CH:19]=5)[CH:27]=[CH:26][N:25]=4)[CH:34]=[CH:33][C:32]=3[N:35]=2)=[O:12])=[CH:9][CH:8]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 701364-(Chloromethyl)benzoyl chlorideHCID 516871Sodium thiocyanateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 220413284-(4-(3-Pyridyl)pyrimidin-2-yloxy)benzene-1,2-diamine

生成物 1

HCID 131725841[4-(Chloromethyl)phenyl]-n-[5-(4-(3-pyridyl)pyrimidin-2-yloxy)benzimidazol-2-yl]carboxamide

試薬・触媒・溶媒 1

HCID 180Acetone溶媒3 回

実験手順

A solution of sodium thiocyanate (1 eq) in acetone was added slowly in to a solution of 4-(chloromethyl)benzoylchloride (1 eq) in acetone at 0° C. The mixture was then filtered in to a solution of 4-(4-(3-pyridyl)pyrimidin-2-yloxy)benzene-1,2-diamine (1 eq) in acetone. Formation of N-acylthiourea was followed by LC/MS. The mixture was concentrated and taken in tetrahydrofuran and to it was added 1-ethyl-(3-dimethylaminopropyl)carbodimidehydrochloride (2 eq) and stirred at ambient temperature for 16 h. The mixture was concentrated and partitioned between ethyl acetate and water. The organic layer was then dried and concentrated to yield [4-(chloromethyl)phenyl]-N-[5-(4-(3-pyridyl)pyrimidin-2-yloxy)benzimidazol-2-yl]carboxamide. It was taken in tetrahydrofuran and added methylpiperazine (4 eq) and stirred at ambient temperature for 16 h. The reaction mixture was concentrated and purified on preparative chromatography to yield {4-[(4-methylpiperazinyl)methyl]phenyl}-N-[5-(4-(3-pyridyl)pyrimidin-2-yloxy)benzimidazol-2-yl]carboxamide. MS: MH+=520.

後処理

  1. concentrationThe mixture was concentrated
  2. concentrationThe mixture was concentrated
  3. custompartitioned between ethyl acetate and water
  4. customThe organic layer was then dried
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-084fb7b4da67426aa581b30a57eee387
出典データセット
uspto-grants-2006_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07071216B2

反応ノート

読み込み中…

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