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

HRID 13473

Reaktionsgleichung

Reaktionsgleichung von HRID 13473
[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

Komponenten

6

Edukt 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

Produkt 1

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

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-[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.

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-145a31cfa28b4bfab5a9bc7ac5183ed4
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728010B2

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