HCID 178494680, compound → HCID 178425891, compound

HRID 1487880Notes

Reaction equation

HRID 1487880 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([CH2:18][O:19]C)[NH:5][C:6]=1[C:7]1[CH:8]=[C:9]([CH:14]=[CH:15][C:16]=1[CH3:17])[C:10]([O:12]C)=[O:11]>Br>[Cl:1][C:2]1[N:3]=[C:4]([CH2:18][OH:19])[NH:5][C:6]=1[C:7]1[CH:8]=[C:9]([CH:14]=[CH:15][C:16]=1[CH3:17])[C:10]([OH:12])=[O:11]

Participants

3

Reactant 1

HCID 178494680HCID 178494680, compound2×

Product 1

HCID 178425891HCID 178425891, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Conditions

Temperature
80 °C

Procedure

Into a 50-mL round-bottom flask, was placed a solution of methyl 3-(4-chloro-2-(methoxymethyl)-1H-imidazol-5-yl)-4-methylbenzoate (compound 27.4, 380 mg, 1.29 mmol, 1.00 equiv) in HBr (40% in AcOH) (10 mL). The solution was stirred overnight at 80° C., then cooled and concentrated under reduced pressure. The crude residue was purified by prep-HPLC (WATER WITH 0.05% TFA and CH3CN (0% CH3CN in 3 min, then up to 100% for 5 min, down to 0% in 1 min); Detector, 254 & 220 nm. The fractions containing clean product were combined and lyophilized to yield 171 mg (50%) of the title compound as yellow crude oil.

Workup

  1. customInto a 50-mL round-bottom flask, was placed
  2. temperaturecooled
  3. concentrationconcentrated under reduced pressure
  4. customThe crude residue was purified by prep-HPLC (WATER WITH 0.05% TFA and CH3CN (0% CH3CN in 3 min
  5. waitup to 100% for 5 min
  6. waitdown to 0% in 1 min)
  7. additionThe fractions containing clean product

Sources & evidence

ORD record
ord-2cb759a1fb104378a79a1f461d6221cb
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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