Hydrochloric Acid → HCID 178497371, compound

HRID 1488094Notes

Reaction equation

HRID 1488094 reaction equation
C([O:8][CH2:9][C:10]1[NH:11][C:12]([C:19]2[C:20]([CH3:30])=[CH:21][C:22]([CH3:29])=[C:23]([CH:28]=2)[C:24]([O:26][CH3:27])=[O:25])=[C:13]([C:15]([F:18])([F:17])[F:16])[N:14]=1)C1C=CC=CC=1.Cl.[H][H]>CO.[Pd]>[OH:8][CH2:9][C:10]1[NH:11][C:12]([C:19]2[C:20]([CH3:30])=[CH:21][C:22]([CH3:29])=[C:23]([CH:28]=2)[C:24]([O:26][CH3:27])=[O:25])=[C:13]([C:15]([F:16])([F:18])[F:17])[N:14]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 178418361HCID 178418361, compoundHCID 178497370HCID 178497370, compound2×

Product 1

HCID 178497371HCID 178497371, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Into a 50-mL round-bottom flask, under a nitrogen atmosphere, was placed a solution of methyl 5-(2-((benzyloxy)methyl)-4-(trifluoromethyl)-1H-imidazol-5-yl)-2,4-dimethylbenzoate (compound 219.3, 150 mg, 0.36 mmol) in methanol (8 mL). Palladium on carbon (150 mg, 1.00 equiv) and HCl (4 M, 2 mL) were added to the reaction under a nitrogen atmosphere. To the above hydrogen (1 atm) was introduced. The reaction mixture was stirred for 2 h at room temperature. The system was purged with nitrogen, then the solids were removed by filtration and the filtrate was concentrated under reduced pressure to give 100 mg (85%) of the title compound as a light yellow oil.

Workup

  1. customInto a 50-mL round-bottom flask, under a nitrogen atmosphere, was placed
  2. customThe system was purged with nitrogen
  3. customthe solids were removed by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-cd7afdf353a44de6a751ea2ee103f167
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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