Potassium Carbonate → [4-(2-Tert-butylaminosulfonylphenyl)phenylaminocarbonyl]methyl-5-cyanobenzimidazole

HRID 1637701Notes

Reaction equation

HRID 1637701 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]2[N:7]=[CH:8][NH:9][C:5]=2[CH:4]=1)#[N:2].[C:12]([NH:16][S:17]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[C:26]1[CH:31]=[CH:30][C:29]([NH:32][C:33]([CH2:35]Cl)=[O:34])=[CH:28][CH:27]=1)(=[O:19])=[O:18])([CH3:15])([CH3:14])[CH3:13].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[C:12]([NH:16][S:17]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[C:26]1[CH:27]=[CH:28][C:29]([NH:32][C:33]([CH2:35][C:8]2[NH:9][C:5]3[CH:4]=[C:3]([C:1]#[N:2])[CH:11]=[CH:10][C:6]=3[N:7]=2)=[O:34])=[CH:30][CH:31]=1)(=[O:18])=[O:19])([CH3:15])([CH3:13])[CH3:14]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2239061H-Benzimidazole-6-carbonitrileHCID 10738598(4-(2-Tert-butylaminosulfonylphenyl)phenyl-aminocarbonyl]methylene chloride

Product 1

HCID 53937819[4-(2-Tert-butylaminosulfonylphenyl)phenylaminocarbonyl]methyl-5-cyanobenzimidazoleYield 37%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Alkylation of 5-cyanobenzimidazole (2 mmol) with [4-(2-tert-butylaminosulfonylphenyl)phenyl-aminocarbonyl]methylene chloride (2 mmol) in DMF (10 mL) and K2CO3 (4 mmol) at r.t. over 16 hours, followed by purification on thin layer TLC plates, and further isolation by HPLC gave [4-(2-tert-butylaminosulfonylphenyl)phenylaminocarbonyl]methyl-6-cyanobenzimidazole (240 mg, 56%) and [4-(2-tert-butylaminosulfonylphenyl)phenylaminocarbonyl]methyl-5-cyanobenzimidazole (160 mg, 37%).

Workup

  1. customfollowed by purification on thin layer TLC plates, and further isolation by HPLC

Sources & evidence

ORD record
ord-955e97f180b442f0bd10ca277c8ce667
Source dataset
uspto-grants-2000_03
Patent number
US06043257

Reaction notes

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