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

HRID 1915654

반응식

HRID 1915654 반응식
[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

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 180Acetone용매3회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7ce54b8bfd5f483fa0da1583ba5208dd
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08614330B2

연결된 노트

불러오는 중…