Methanesulfonyl chloride → methanesulfonic acid 4-bromo-2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazol-5-ylmethyl ester

HRID 1661943Notes

Reaction equation

HRID 1661943 reaction equation
[Br:1][C:2]1[C:10]2[N:9]=[C:8]([C:11]3[CH:16]=[CH:15][C:14]([CH:17]([CH3:19])[CH3:18])=[CH:13][CH:12]=3)[N:7]([CH2:20][CH2:21][O:22][CH3:23])[C:6]=2[C:5]([O:24][CH3:25])=[CH:4][C:3]=1[CH2:26][OH:27].[CH3:28][S:29](Cl)(=[O:31])=[O:30].CCN(C(C)C)C(C)C>C(Cl)Cl>[Br:1][C:2]1[C:10]2[N:9]=[C:8]([C:11]3[CH:12]=[CH:13][C:14]([CH:17]([CH3:19])[CH3:18])=[CH:15][CH:16]=3)[N:7]([CH2:20][CH2:21][O:22][CH3:23])[C:6]=2[C:5]([O:24][CH3:25])=[CH:4][C:3]=1[CH2:26][O:27][S:29]([CH3:28])(=[O:31])=[O:30]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 57771990[4-bromo-2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazol-5-yl]-methanol

Product 1

HCID 57771995methanesulfonic acid 4-bromo-2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazol-5-ylmethyl esterYield 101.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 200 mg (0.462 mmol) [4-Bromo-2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazol-5-yl]-methanol is dissolved in 5 ml CH2Cl2. The solution is cooled to 0° C. and methanesulfonyl chloride (47 ul, 0.600 mmol) and Huenig's base (103 ul, 0.600 mmol) is added. After 1 h the reaction is extracted with CH2Cl2/10% citric acid. The organic layer is dried over MgSO4, filtered and concentrated in vacuo to give 240 mg of material which is used without further purification.

Workup

  1. extractionAfter 1 h the reaction is extracted with CH2Cl2/10% citric acid
  2. dry with materialThe organic layer is dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d10f36f1d4944a81b1927a369874fac8
Source dataset
uspto-grants-2011_10
Patent number
US08030497B2

Reaction notes

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