4-Chlorobenzaldehyde → HCID 86707785, compound

HRID 2410142Notes

Reaction equation

HRID 2410142 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([Br:23])[N:9]([CH:20]([CH3:22])[CH3:21])[C:10]=1[CH:11]([C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)[OH:12])=[O:5])[CH3:2].ClC1C=CC([CH:29]=[O:30])=CC=1>>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([Br:23])[N:9]([C@H:20]([CH3:22])[CH2:21][O:30][CH3:29])[C:10]=1[CH:11]([C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)[OH:12])=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 77264-ChlorobenzaldehydeHCID 86707749ethyl 2-bromo-5-((4-chlorophenyl)(hydroxy)methyl)-1-isopropyl-1H-imidazole-4-carboxylate

Product 1

HCID 86707785HCID 86707785, compound

Procedure

The title compound was obtained in analogy to the procedure described for intermediate B but using 4-chlorobenzaldehyde and the product from step 256.5. After completion, the reaction mixture was quenched with a 1M NH4Cl solution and extracted with EtOAc. The organic layer was dried (Na2SO4), filtered and concentrated. The residue was purified by flas chromatography (heptane/EtOAc, 80:20→20:80) to give the title compound. tR: 1.08 min (LC-MS 2); ESI-MS: 431.1/433.0 [M+H]+ (LC-MS 2).

Workup

  1. customAfter completion, the reaction mixture was quenched with a 1M NH4Cl solution
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flas chromatography (heptane/EtOAc, 80:20→20:80)

Sources & evidence

ORD record
ord-e4e06ebd799c4d9aa45c41199c3b3d1d
Source dataset
uspto-grants-2014_08
Patent number
US08815926B2

Reaction notes

Loading…