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

HRID 1915654

Reaktionsgleichung

Reaktionsgleichung von HRID 1915654
[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

Komponenten

6

Edukt 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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel3×

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-7ce54b8bfd5f483fa0da1583ba5208dd
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08614330B2

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