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

HRID 1915649

Reaction equation

HRID 1915649 reaction equation
[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

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent3×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-1bc9c99db8ec4c1fae5a4f6ff718ed37
Source dataset
uspto-grants-2013_12
Patent number
US08614330B2

Linked notes

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