2'-Methanesulfonyl-biphenyl-3,4-diamine → HCID 178504704, compound

HRID 1433192Notes

Reaction equation

HRID 1433192 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[CH:16]=[CH:15][C:14]([NH2:17])=[C:13]([NH2:18])[CH:12]=1)(=[O:4])=[O:3].Cl.C(O[C:23](=N)[CH2:24][Br:25])C>C(O)C>[Br:25][CH2:24][C:23]1[NH:17][C:14]2[CH:15]=[CH:16][C:11]([C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=3[S:2]([CH3:1])(=[O:3])=[O:4])=[CH:12][C:13]=2[N:18]=1

Participants

4

Reactant 2

HCID 579349992'-Methanesulfonyl-biphenyl-3,4-diamineHCID 75357914Ethyl 2-bromoethanecarboximidate hydrochloride

Product 1

HCID 178504704HCID 178504704, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2′-methanesulfonyl-biphenyl-3,4-diamine (8.09 g, 0.0308 mol) and 2-bromoacetimidic acid ethyl ester hydrochloride salt (11.82 g, 0.0370 mol) in anhydrous ethanol (200 proof, 120 mL) was stirred at room temperature for 12 h. The reaction mixture was concentrated under reduced pressure and extracted with ethyl acetate and brine. The organic layer was dried over Na2SO4, filtered, and the filtrate was concentrated in vacuo to provide 2-bromomethyl-5-(2-methanesulfonyl-phenyl)-1H-benzoimidazole (10.36 g, 92%) as a yellow oil. To a solution of this material in CH2Cl2, was added Boc2O (7.39 g, 0.0339 mol), Et3N (12.9 mL, 0.0924 mol), and DMAP (0.19 g, 0.00154 mol). After stirring 1 h at room temperature, the reaction mixture was concentrated under reduced pressure and the residue was purified by chromatography (silica, EtOAc: hexanes, 1:2) to afford the title compound as a yellow oil (10.17 g, 77%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionextracted with ethyl acetate and brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-e8fd954ca50a445c9c9e8a81dadd70dc
Source dataset
uspto-grants-2009_11
Patent number
US07612211B2

Reaction notes

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