HCID 135872764, compound → HCID 136338458, compound

HRID 1157959Notes

Reaction equation

HRID 1157959 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[C:8]([O:12][C:13](=[O:55])[NH:14][CH2:15][C:16]1[CH:21]=[C:20]([NH:22][CH:23]([C:39]2[CH:44]=[C:43]([CH2:45][CH3:46])[CH:42]=[C:41]([O:47][CH2:48][CH2:49][N:50]([CH3:52])[CH3:51])[C:40]=2[F:53])[C:24]2[NH:28][C:27](=[O:29])[N:26]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[N+:36]([O-])=O)[N:25]=2)[CH:19]=[CH:18][C:17]=1[Br:54])([CH3:11])([CH3:10])[CH3:9]>[Fe].CO.C(O)(=O)C.O>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[C:8]([O:12][C:13](=[O:55])[NH:14][CH2:15][C:16]1[CH:21]=[C:20]([NH:22][CH:23]([C:24]2[NH:28][C:27](=[O:29])[N:26]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[NH2:36])[N:25]=2)[C:39]2[CH:44]=[C:43]([CH2:45][CH3:46])[CH:42]=[C:41]([O:47][CH2:48][CH2:49][N:50]([CH3:52])[CH3:51])[C:40]=2[F:53])[CH:19]=[CH:18][C:17]=1[Br:54])([CH3:9])([CH3:10])[CH3:11]

Participants

4

Reactant 1

HCID 135872764HCID 135872764, compound

Product 1

HCID 136338458HCID 136338458, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 86607755Acetic acid methanol waterSolvent

Conditions

Temperature
60 °C

Procedure

Iron powder (70 mg) was added to [2-bromo-5-({[3-(2-dimethylaminoethoxy)-5-ethyl-2-fluorophenyl]-[1-(2-nitrophenyl)-5-oxo-4,5-dihydro-1H-[1,2,4]triazol-3-yl]methyl}amino)benzyl] carbamic acid t-butyl ester trifluoroacetic acid salt (76 mg) and a methanol:acetic acid:water (1:1:1) mixed solvent (6 mL) under a nitrogen atmosphere, and the mixture was heated for 18 hours at 60° C. 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 reverse-phase high performance liquid chromatography (acetonitrile/water mixed solvent, 0.1% trifluoroacetic acid) to obtain the target compound (44 mg) as a colorless oil.

Workup

  1. filtrationThe mixture was filtered
  2. customto obtain a filtrate
  3. distillationthe solvent in the filtrate was distilled off under reduced pressure
  4. customThe residue was purified by reverse-phase high performance liquid chromatography (acetonitrile/water mixed solvent, 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-84d49f98bf774220993815c2681098a7
Source dataset
uspto-grants-2010_10
Patent number
US07807690B2

Reaction notes

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