1-Methylpiperazine → n-Methyl {4-[1-methyl-2-({4-[(4-methylpiperazinyl)methyl]phenyl}carbonylamino)benzimidazol-5-yloxy](2-pyridyl)}carboxamide

HRID 2070275Notes

Reaction equation

HRID 2070275 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([NH:11][C:12]2[N:16]([CH3:17])[C:15]3[CH:18]=[CH:19][C:20]([O:22][C:23]4[CH:28]=[CH:27][N:26]=[C:25]([C:29]([NH:31][CH3:32])=[O:30])[CH:24]=4)=[CH:21][C:14]=3[N:13]=2)=[O:10])=[CH:5][CH:4]=1.[CH3:33][N:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1>O1CCCC1>[CH3:32][NH:31][C:29]([C:25]1[CH:24]=[C:23]([O:22][C:20]2[CH:19]=[CH:18][C:15]3[N:16]([CH3:17])[C:12]([NH:11][C:9]([C:6]4[CH:7]=[CH:8][C:3]([CH2:2][N:37]5[CH2:38][CH2:39][N:34]([CH3:33])[CH2:35][CH2:36]5)=[CH:4][CH:5]=4)=[O:10])=[N:13][C:14]=3[CH:21]=2)[CH:28]=[CH:27][N:26]=1)=[O:30]

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 131725840[4-(2-{[4-(Chloromethyl)phenyl]carbonylamino}-1-methylbenzimidazol-5-yloxy)(2-pyridyl)]-n-methylcarboxamide

Product 1

HCID 22040418n-Methyl {4-[1-methyl-2-({4-[(4-methylpiperazinyl)methyl]phenyl}carbonylamino)benzimidazol-5-yloxy](2-pyridyl)}carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [4-(2-{[4-(chloromethyl)phenyl]carbonylamino)-1-methylbenzimidazol-5-yloxy)(2-pyridyl)]-N-methylcarboxamide (1 eq) in tetrahydrofuran was added methylpiperazine (4 eq) and stirred at ambient temperature for 16 h. The reaction mixture was concentrated and purified on preparative chromatography to yield N-methyl{4-[1-methyl-2-({4-[(4methylpiperazinyl) methyl]phenyl}carbonylamino) benzimidazol-5-yloxy](2-pyridyl)}carboxamide. MS: MH+=512.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified on preparative chromatography

Sources & evidence

ORD record
ord-eae559966b87491a9d4f85fcf1ffaed1
Source dataset
uspto-grants-2012_10
Patent number
US08299108B2

Reaction notes

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