ethyl 2-bromo-5-((4-chlorophenyl)(hydroxy)methyl)-1-isopropyl-1H-imidazole-4-carboxylate → 2-Bromo-5-[(5-chloro-2-oxo-1,2-dihydro-pyridin-3-ylamino)-(4-chloro-phenyl)-methyl]-1-isopropyl-1H-imidazole-4-carboxylic acid ethyl ester

HRID 2410134Notes

Reaction equation

HRID 2410134 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)O)=[O:5])[CH3:2].[NH2:24][C:25]1[C:26]([OH:32])=[N:27][CH:28]=[C:29]([Cl:31])[CH:30]=1>>[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]([NH:24][C:25]1[C:26](=[O:32])[NH:27][CH:28]=[C:29]([Cl:31])[CH:30]=1)[C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 86707749ethyl 2-bromo-5-((4-chlorophenyl)(hydroxy)methyl)-1-isopropyl-1H-imidazole-4-carboxylateHCID 178507679HCID 178507679, compound

Product 1

HCID 867077792-Bromo-5-[(5-chloro-2-oxo-1,2-dihydro-pyridin-3-ylamino)-(4-chloro-phenyl)-methyl]-1-isopropyl-1H-imidazole-4-carboxylic acid ethyl ester

Procedure

The title compound was prepared in analogy to the procedure described for step E2 but using intermediate B and 3-amino-5-chloropyridin-2-ol. The reaction mixture was quenched with a saturated aqueous NaHCO3 solution and extracted with EtOAc. The organic layer was washed with a saturated aqueous NaHCO3 solution, dried (Na2SO4), filtered and concentrated. The product was purified by flash chromatography (CH2Cl2/MeOH, 99:1→97:3). tR: 1.15-1.18 min (LC-MS 2); ESI-MS: 527.1/529.1/531.1 [M+H]+ (LC-MS 2); Rf: 0.41 (CH2Cl2/MeOH 9:1).

Workup

  1. customThe reaction mixture was quenched with a saturated aqueous NaHCO3 solution
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with a saturated aqueous NaHCO3 solution
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe product was purified by flash chromatography (CH2Cl2/MeOH, 99:1→97:3)

Sources & evidence

ORD record
ord-3f1ed35069a445bdbcde8003b215b276
Source dataset
uspto-grants-2014_08
Patent number
US08815926B2

Reaction notes

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