Hydrochloric Acid → HCID 178469991, compound

HRID 408786Notes

Reaction equation

HRID 408786 reaction equation
Cl.[CH2:2]([O:4][C:5]([C:7]1[CH:8]=[N:9][N:10]([C:12]2[N:16](COCCOC)[C:15]3[CH:23]=[C:24]([Cl:37])[C:25]([S:27](=[O:36])(=[O:35])[NH:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[CH:26][C:14]=3[N:13]=2)[CH:11]=1)=[O:6])[CH3:3]>O1CCOCC1.C(O)C>[CH2:2]([O:4][C:5]([C:7]1[CH:8]=[N:9][N:10]([C:12]2[NH:16][C:15]3[CH:23]=[C:24]([Cl:37])[C:25]([S:27](=[O:36])(=[O:35])[NH:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[CH:26][C:14]=3[N:13]=2)[CH:11]=1)=[O:6])[CH3:3]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 66937310HCID 66937310, compound

Product 1

HCID 178469991HCID 178469991, compoundYield 98.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
23 °C

Procedure

Hydrochloric acid in dioxane (4M, 0.241 mL) was added to 1-[6-chloro-1-(2-methoxy-ethoxymethyl)-5-phenylsulfamoyl-1H-benzoimidazol-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester (35.0 mg, 65.5 μmol) in ethanol (0.50 mL) and allowed to stir at 23° C. for 2.5 h. The solvent was evaporated and the residue was purified via FCC (5-100% EtOAc/hexanes) to yield the titled compound (28.7 mg, 98% yield). MS (ESI/CI): mass calcd. for C19H16ClN5O4S, 445.1; m/z found, 446.0 [M+H]+.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified via FCC (5-100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-8297041bcb8d41eb9cea4d07772b26ca
Source dataset
uspto-grants-2014_06
Patent number
US08759345B2

Reaction notes

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