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

HRID 1915649

반응식

HRID 1915649 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.[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

참가 물질

6

반응물 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

생성물 1

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

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-[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.

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-1bc9c99db8ec4c1fae5a4f6ff718ed37
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08614330B2

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