Acetic Acid → HCID 71117429, compound

HRID 2368521Notes

Reaction equation

HRID 2368521 reaction equation
[NH2:1][C:2]1[N:3]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[C:4]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][N:6]=1.[F:18][C:19]1[C:26]([F:27])=[CH:25][CH:24]=[C:23]([F:28])[C:20]=1[CH:21]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>C(#N)C>[F:17][C:14]1[CH:15]=[CH:16][C:11]([N:3]2[C:4]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][N:6]=[C:2]2[NH:1][CH2:21][C:20]2[C:23]([F:28])=[CH:24][CH:25]=[C:26]([F:27])[C:19]=2[F:18])=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5178452,3,6-TrifluorobenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 71117564HCID 71117564, compound

Product 1

HCID 71117429HCID 71117429, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Methyl 2-amino-1-(4-fluorophenyl)-1H-imidazole-5-carboxylate (67) (200 mg, 0.85 mmol), 2,3,6-trifluorobenzaldehyde (163 mg, 1.02 mmol), sodium triacetoxyborohydride (450 mg, 2.13 mmol) and catalytic amounts of acetic acid in acetonitrile (5 mL) was heated under microwave radiation for 2 hours. The reaction mixture was quenched with saturated sodium bicarbonate solution and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (0-100% EtOAc in hexanes) to afford methyl 1-(4-fluorophenyl)-2-((2,3,6-trifluorobenzyl)amino)-1H-imidazole-5-carboxylate (68).

Workup

  1. customThe reaction mixture was quenched with saturated sodium bicarbonate solution
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography on silica gel (0-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-b80d75f2f3c94cb8963bef21079d3993
Source dataset
uspto-grants-2014_04
Patent number
US08703776B2

Reaction notes

Loading…