HCID 136338459, compound → HCID 135999739, compound

HRID 1157964Notes

Reaction equation

HRID 1157964 reaction equation
[C:1]([O:5][C:6](=[O:44])[NH:7][CH2:8][C:9]1[CH:14]=[C:13]([NH:15][CH:16]([C:32]2[CH:37]=[C:36]([O:38][CH3:39])[C:35]([O:40][CH3:41])=[CH:34][C:33]=2[F:42])[C:17]2[NH:21][C:20](=[O:22])[N:19]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[N+:29]([O-])=O)[N:18]=2)[CH:12]=[CH:11][C:10]=1[Br:43])([CH3:4])([CH3:3])[CH3:2]>[Fe].CO.C(O)(=O)C.O>[C:1]([O:5][C:6](=[O:44])[NH:7][CH2:8][C:9]1[CH:14]=[C:13]([NH:15][CH:16]([C:17]2[NH:21][C:20](=[O:22])[N:19]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[NH2:29])[N:18]=2)[C:32]2[CH:37]=[C:36]([O:38][CH3:39])[C:35]([O:40][CH3:41])=[CH:34][C:33]=2[F:42])[CH:12]=[CH:11][C:10]=1[Br:43])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 136338459HCID 136338459, compound

Product 1

HCID 135999739HCID 135999739, compoundYield 66.3%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 86607755Acetic acid methanol waterSolvent

Conditions

Temperature
60 °C

Procedure

Iron powder (231 mg) was added to [2-bromo-5-({(2-fluoro-4,5-dimethoxyphenyl)-[1-(2-nitrophenyl)-5-oxo-4,5-dihydro-1H-[1,2,4]triazol-3-yl]methyl}amino)benzyl]carbamic acid t-butyl ester (232 mg) and a methanol:acetic acid:water (1:1:1) mixed solvent (24 mL), and the mixture was heated for 18 hours at 60° C. under a nitrogen atmosphere. The solvent in the mixture was distilled off under reduced pressure, and ethyl acetate (100 mL) and water (25 mL) were added to the residue. Sodium hydrogen carbonate was gradually added to the mixture to adjust the pH to 8. After sufficiently shaking the mixture, the organic layer was separated off and dried over anhydrous magnesium sulfate. The mixture was filtered to obtain a filtrate, and the solvent in the filtrate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-heptane mixture) to obtain the target compound (147 mg) as an off-white solid.

Workup

  1. distillationThe solvent in the mixture was distilled off under reduced pressure, and ethyl acetate (100 mL) and water (25 mL)
  2. additionwere added to the residue
  3. additionSodium hydrogen carbonate was gradually added to the mixture
  4. customthe organic layer was separated off
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationThe mixture was filtered
  7. customto obtain a filtrate
  8. distillationthe solvent in the filtrate was distilled off under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (ethyl acetate-heptane mixture)

Sources & evidence

ORD record
ord-886283248074435ba88f4cb34dc65936
Source dataset
uspto-grants-2010_10
Patent number
US07807690B2

Reaction notes

Loading…