Methanesulfonyl chloride → 4-(3-Chloro-phenyl)-2-[6-(4-methanesulfonyloxy-butyl)-benzoimidazol-1-yl]-thiazole-5-carboxylic acid ethyl ester

HRID 1667765Notes

Reaction equation

HRID 1667765 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([N:11]2[C:15]3[CH:16]=[C:17]([CH2:20][CH2:21][CH2:22][CH2:23][OH:24])[CH:18]=[CH:19][C:14]=3[N:13]=[CH:12]2)=[N:8][C:7]=1[C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[CH:26]=1)=[O:5])[CH3:2].C(N(C(C)C)C(C)C)C.[CH3:41][S:42](Cl)(=[O:44])=[O:43]>ClCCl>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([N:11]2[C:15]3[CH:16]=[C:17]([CH2:20][CH2:21][CH2:22][CH2:23][O:24][S:42]([CH3:41])(=[O:44])=[O:43])[CH:18]=[CH:19][C:14]=3[N:13]=[CH:12]2)=[N:8][C:7]=1[C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[CH:26]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 674467194-(3-Chloro-phenyl)-2-[6-(4-hydroxy-butyl)-benzoimidazol-1-yl]-thiazole-5-carboxylic acid ethyl ester

Product 1

HCID 866428384-(3-Chloro-phenyl)-2-[6-(4-methanesulfonyloxy-butyl)-benzoimidazol-1-yl]-thiazole-5-carboxylic acid ethyl esterYield 79.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 0.266 g (0.583 mmole) of 4-(3-chloro-phenyl)-2-[6-(4-hydroxy-butyl)-benzoimidazol-1-yl]-thiazole-5-carboxylic acid ethyl ester (I.41d), 0.152 mL (0.875 mmole) of ethyldiisopropylamine and 5 mL of dichloromethane at 0 degrees was added 0.054 mL (0.7 mmole) of methanesulfonyl chloride. The mixture was stirred at ambient temperature for 1 hour and then diluted with 30 mL of dichloromethane. The mixture was washed with 10 mL of saturated sodium bicarbonate, brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography, eluting with methanol-dichloromethane (gradient 0:100-2:98) to give 0.248 g of 4-(3-chloro-phenyl)-2-[6-(4-methanesulfonyloxy-butyl)-benzoimidazol-1-yl]-thiazole-5-carboxylic acid ethyl ester (I.41e) as a yellow solid.

Workup

  1. washThe mixture was washed with 10 mL of saturated sodium bicarbonate, brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with methanol-dichloromethane (gradient 0:100-2:98)

Sources & evidence

ORD record
ord-b0c9bdd1286648ada72a8721ce764e99
Source dataset
uspto-grants-2011_10
Patent number
US08044213B2

Reaction notes

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