Hydrochloric Acid → HCID 66937073, compound

HRID 408682Notes

Reaction equation

HRID 408682 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:11]2[N:15](COCCOC)[C:14]3[CH:22]=[CH:23][CH:24]=[C:25]([Cl:26])[C:13]=3[N:12]=2)[CH:10]=1)=[O:5])[CH3:2].Cl.O1CCOCC1>CCO>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:11]2[NH:15][C:14]3[CH:22]=[CH:23][CH:24]=[C:25]([Cl:26])[C:13]=3[N:12]=2)[CH:10]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 66937166HCID 66937166, compound

Product 1

HCID 66937073HCID 66937073, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
23 °C

Procedure

To a mixture of 1-[4-chloro-1-(2-methoxy-ethoxymethyl)-1H-benzoimidazol-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester (0.370 g, 0.980 mmol) and EtOH (2.5 mL), was added 4M HCl in dioxane (2.5 mL, 10 mmol). The mixture was stirred for 18 h at 23° C. The resulting white precipitate was filtered and washed with EtOH to yield the titled compound (0.260 g, 93%). MS (ESI/CI): mass calcd. for C13H11ClN4O2, 290.1; m/z found, 291.1 [M+H]+. 1H NMR (500 MHz, DMSO-d6): 13.83 (s, 1H), 8.98 (s, 1H), 8.45-8.29 (m, 1H), 7.46 (s, 1H), 7.38-7.16 (m, 2H), 4.59-4.01 (m, 2H), 1.60-1.01 (m, 3H).

Workup

  1. filtrationThe resulting white precipitate was filtered
  2. washwashed with EtOH

Sources & evidence

ORD record
ord-111d791bf8db49549ed3792c5fffa328
Source dataset
uspto-grants-2014_06
Patent number
US08759345B2

Reaction notes

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