Methanesulfonyl chloride → methanesulfonic acid 2-(3-isopropyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-1-(3-methyl-butyl)-1H-benzoimidazol-5-ylmethyl ester

HRID 896306Notes

Reaction equation

HRID 896306 reaction equation
[OH:1][CH2:2][C:3]1[CH:30]=[CH:29][C:6]2[N:7]([CH2:24][CH2:25][CH:26]([CH3:28])[CH3:27])[C:8]([CH2:10][N:11]3[C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=4[N:13]([CH:20]([CH3:22])[CH3:21])[C:12]3=[O:23])=[N:9][C:5]=2[CH:4]=1.[CH3:31][S:32](Cl)(=[O:34])=[O:33]>C(Cl)Cl>[CH:20]([N:13]1[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N:11]([CH2:10][C:8]2[N:7]([CH2:24][CH2:25][CH:26]([CH3:28])[CH3:27])[C:6]3[CH:29]=[CH:30][C:3]([CH2:2][O:1][S:32]([CH3:31])(=[O:34])=[O:33])=[CH:4][C:5]=3[N:9]=2)[C:12]1=[O:23])([CH3:21])[CH3:22]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 208140091-[5-hydroxymethyl-1-(3-methyl-butyl)-1H-benzoimidazol-2-ylmethyl]-3-isopropyl-1,3-dihydro-benzoimidazol-2-one

Product 1

HCID 20813972methanesulfonic acid 2-(3-isopropyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-1-(3-methyl-butyl)-1H-benzoimidazol-5-ylmethyl esterYield 33.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-[5-hydroxymethyl-1-(3-methyl-butyl)-1H-benzoimidazol-2-ylmethyl]-3-isopropyl-1,3-dihydro-benzoimidazol-2-one (155 mg, 0.38 mmol) and TEA (130 mg, 1.14 mmol) in DCM (5 mL) was added methanesulfonyl chloride (87 mg, 0.76 mmol) at 0° C. The final solution was stirred at ambient temperature for 12 h then washed with sat. NaHCO3 and brine. The organic layer was dried with MgSO4 and evaporated. The residue was purified by flash chromatography (hexanes:EtOAc 2:1 to 1:1) to give 62 mg (33%) of methanesulfonic acid 2-(3-isopropyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-1-(3-methyl-butyl)-1H-benzoimidazol-5-ylmethyl ester as a white solid.

Workup

  1. washthen washed with sat. NaHCO3 and brine
  2. dry with materialThe organic layer was dried with MgSO4
  3. customevaporated
  4. customThe residue was purified by flash chromatography (hexanes:EtOAc 2:1 to 1:1)

Sources & evidence

ORD record
ord-711cbe6e1ba24cac8148099e5ca9226c
Source dataset
uspto-grants-2005_07
Patent number
US06919331B2

Reaction notes

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