4-(Chloromethyl)benzoyl chloride → [4-(2-{[4-(Chloromethyl)phenyl]carbonylamino}-1-methylbenzimidazol-5-yloxy)(2-pyridyl)]-n-methylcarboxamide

HRID 1790682

反応式

HRID 1790682 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.[NH2:16][C:17]1[CH:18]=[C:19]([CH:31]=[CH:32][C:33]=1[NH:34][CH3:35])[O:20][C:21]1[CH:26]=[CH:25][N:24]=[C:23]([C:27](NC)=[O:28])[CH:22]=1.Cl.[CH2:37]([N:39]=C=NCCCN(C)C)C>CC(C)=O>[Cl:5][CH2:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([NH:39][C:37]2[N:34]([CH3:35])[C:33]3[CH:32]=[CH:31][C:19]([O:20][C:21]4[CH:26]=[CH:25][N:24]=[C:23]([C:27]([NH:3][CH3:2])=[O:28])[CH:22]=4)=[CH:18][C:17]=3[N:16]=2)=[O:12])=[CH:9][CH:8]=1

参加物

6

反応物 4

HCID 701364-(Chloromethyl)benzoyl chlorideHCID 516871Sodium thiocyanateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 177558384-(3-Amino-4-methylamino-phenoxy)-pyridine-2-carboxylic acid methylamide

生成物 1

HCID 131725840[4-(2-{[4-(Chloromethyl)phenyl]carbonylamino}-1-methylbenzimidazol-5-yloxy)(2-pyridyl)]-n-methylcarboxamide

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-[3-amino-4-(methylamino)phenoxy](2-pyridyl)}-N-methylcarboxamide (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-(2-{[4-(chloromethyl)phenyl]carbonylamino}-1-methylbenzimidazol-5-yloxy)(2-pyridyl)]-N-methylcarboxamide. MS: MH+=449.

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-0a79efa2b0854b679e5635cea251931d
出典データセット
uspto-grants-2006_07
特許番号
US07071216B2

関連ノート

読み込み中…