HCID 178497722, compound → HCID 178425890, compound

HRID 1488219Notes

Reaction equation

HRID 1488219 reaction equation
[OH:1][CH2:2][C:3]1[NH:4][C:5]([C:12]2[CH:13]=[C:14]([CH:19]=[CH:20][C:21]=2[CH3:22])[C:15]([O:17]C)=[O:16])=[C:6]([C:8]([F:11])([F:10])[F:9])[N:7]=1>Br>[OH:1][CH2:2][C:3]1[NH:4][C:5]([C:12]2[CH:13]=[C:14]([CH:19]=[CH:20][C:21]=2[CH3:22])[C:15]([OH:17])=[O:16])=[C:6]([C:8]([F:9])([F:11])[F:10])[N:7]=1

Participants

3

Reactant 1

HCID 178497722HCID 178497722, compound2×

Product 1

HCID 178425890HCID 178425890, compoundYield 52.4%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Conditions

Temperature
80 °C

Procedure

Into a 100-mL round-bottom flask, was placed methyl 3-(2-(hydroxymethyl)-4-(trifluoromethyl)-1H-imidazol-5-yl)-4-methylbenzoate (compound 284.1, 2 g, 6.36 mmol), HBr (40% in AcOH) (50 mL). The reaction mixture was stirred for 12 h at 80° C. The crude product (100 mL) was purified by Flash-Prep-HPLC with the following conditions (IntelFlash-1): mobile phase, CH3CN:H2O=1:1; Detector, UV 254 nm to yield 1 g (52%) of the title compound as a light yellow solid.

Workup

  1. customInto a 100-mL round-bottom flask, was placed
  2. customThe crude product (100 mL) was purified by Flash-Prep-HPLC with the following conditions (IntelFlash-1)

Sources & evidence

ORD record
ord-9070947f64794209b389b0df763e4580
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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