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

HRID 1419608
Notes
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Reaction equation

HRID 1419608 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 6228
Dimethylformamide
Solvent

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-4dbee1b5a5ac4b4dbacd9b129e39adb8
Source dataset
uspto-grants-1999_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05886191

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes