Methanesulfonyl chloride → HCID 57772049, compound

HRID 1661923Notes

Reaction equation

HRID 1661923 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:14]([CH2:15][CH2:16][O:17][CH3:18])[C:13]3[C:19]([O:31][CH3:32])=[CH:20][C:21]([CH:23]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=4)[OH:24])=[CH:22][C:12]=3[N:11]=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].C(N(C(C)C)C(C)C)C.[CH3:42][S:43](Cl)(=[O:45])=[O:44]>>[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:14]([CH2:15][CH2:16][O:17][CH3:18])[C:13]3[C:19]([O:31][CH3:32])=[CH:20][C:21]([CH:23]([O:24][S:43]([CH3:42])(=[O:45])=[O:44])[C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=4)=[CH:22][C:12]=3[N:11]=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 57772075HCID 57772075, compound

Product 1

HCID 57772049HCID 57772049, compound

Conditions

Temperature
0 °C

Procedure

A mixture of 330 mg (0.76 mmol) [2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazol-5-yl]-pyridin-2-yl-methanol, 0.6 ml ethyl-diisopropyl-amine and 0.25 ml methanesulfonyl chloride is stirred at 0° C. for 1 h. Then the reaction mixture is poured on water and extracted (3×) with ethyl acetate. The combined organic layers are washed with water and brine, dried over MgSO4, filtered and concentrated in vacuo to afford the title product as an oil that is used directly in the next step.

Workup

  1. additionThen the reaction mixture is poured on water
  2. extractionextracted (3×) with ethyl acetate
  3. washThe combined organic layers are washed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-799272515064479394b7bc868966087f
Source dataset
uspto-grants-2011_10
Patent number
US08030497B2

Reaction notes

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