Methanesulfonyl chloride → HCID 57785826, compound

HRID 1628612Notes

Reaction equation

HRID 1628612 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:13]([CH2:14][CH2:15]O)[C:12]3[C:17]([CH:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[CH:18][CH:19]=[C:20]([Cl:21])[C:11]=3[N:10]=2)=[C:4]([Cl:27])[CH:3]=1.CS(Cl)(=O)=O>N1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:9]3=[N:10][C:11]4[C:20]([Cl:21])=[CH:19][CH:18]=[C:17]([CH:22]([CH2:25][CH3:26])[CH2:23][CH3:24])[C:12]=4[N:13]3[CH2:14][CH2:15]2)=[C:4]([Cl:27])[CH:3]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 68767091HCID 68767091, compound

Product 1

HCID 57785826HCID 57785826, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2-[2-[(4-bromo-2-chlorophenyl)amino]-4-chloro-7-(1-ethylpropyl)-1H-benzimidazol-1-yl]ethanol (Reference Example 23; 1.19 g, 2.53 mmol) in pyridine (6.0 mL) was added methanesulfonyl chloride (979 μL, 12.65 mmol) at 0° C. The reaction mixture was stirred at room temperature for 1.5 hr. The reaction mixture was quenched with saturated aqueous sodium hydrogen carbonate at 0° C. and extracted with ethyl acetate (×3). The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with a 0-15% ethyl acetate/n-hexane gradient mixture to give a solid. The resulting solid was recrystallized from n-hexane to give the title compound as a colorless powder (975.2 mg, 2.15 mmol, 85%).

Workup

  1. customThe reaction mixture was quenched with saturated aqueous sodium hydrogen carbonate at 0° C.
  2. extractionextracted with ethyl acetate (×3)
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography
  8. washeluting with a 0-15% ethyl acetate/n-hexane gradient mixture
  9. customto give a solid
  10. customThe resulting solid was recrystallized from n-hexane

Sources & evidence

ORD record
ord-4628fcc33c8f472896f1c59ada9631be
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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