Hydrochloric Acid → HCID 178433400, compound

HRID 241457Notes

Reaction equation

HRID 241457 reaction equation
[F:1][CH:2]([F:19])[C:3]1[N:8]=[CH:7][C:6]([C:9]2[NH:13][C:12]([NH:14]C(=O)C)=[N:11][C:10]=2[CH3:18])=[CH:5][CH:4]=1.Cl>CO.O>[F:19][CH:2]([F:1])[C:3]1[N:8]=[CH:7][C:6]([C:9]2[NH:13][C:12]([NH2:14])=[N:11][C:10]=2[CH3:18])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178474433HCID 178474433, compound

Product 1

HCID 178433400HCID 178433400, compoundYield 105%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Dissolve N-[5-[6-(difluoromethyl)-3-pyridyl]-4-methyl-1H-imidazol-2-yl]acetamide (0.172 g, 0.65 mmol) in MeOH (5 mL) and water (5 mL). Heat the mixture to 60° C. Add hydrochloric acid (12 N, 5 mL, 60 mmol). Stir mixture for 2 hours at 60° C. Concentrate the mixture to a volume of about 10 mL. Adjust the pH of the aqueous solution to 8. Extract the resulting solution with EtOAc (2×20 mL). Dry the combined organic extracts over sodium sulfate; filter; collect the filtrate; and concentrate the filtrate under reduced pressure to give the title compound as a yellow oil (0.153 g, 100% crude yield). LCMS (m/z) 225 (M+1).

Workup

  1. concentrationConcentrate the mixture to a volume of about 10 mL
  2. extractionExtract the resulting solution with EtOAc (2×20 mL)
  3. dry with materialDry the combined organic extracts over sodium sulfate
  4. filtrationfilter
  5. customcollect the filtrate
  6. concentrationand concentrate the filtrate under reduced pressure

Sources & evidence

ORD record
ord-680f169aa1f44a10b1c5997d55b30285
Source dataset
uspto-grants-2014_02
Patent number
US08648200B2

Reaction notes

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