HCID 57770761, compound → HCID 57770854, compound

HRID 2092623Notes

Reaction equation

HRID 2092623 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)[CH:8]=[C:9]([NH:11][NH2:12])[CH:10]=1)=[O:4].CN([CH:23]=[N:24][C:25](=O)[CH:26]([CH3:28])[CH3:27])C>CC(O)=O>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)[CH:8]=[C:9]([N:11]2[C:25]([CH:26]([CH3:28])[CH3:27])=[N:24][CH:23]=[N:12]2)[CH:10]=1)=[O:4]

Participants

4

Reactant 2

HCID 57770761HCID 57770761, compoundHCID 57770793HCID 57770793, compound

Product 1

HCID 57770854HCID 57770854, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 5-hydrazino-4′-methyl-biphenyl-3-carboxylic acid methyl ester (300 mg, 1.17 mmol) in HOAc (5 mL) was added N-dimethylaminomethylene-isobutyramide (233 mg. 1.4 mmol) in one portion. The mixture was heated to 90° C. for two hours. After removing the excess HOAc, the residue was dissolved in EtOAc and washed with saturated aqueous NaHCO3. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography (ISCO™) to afford 5-(5-isopropyl-[1,2,4]triazol-1-yl)-4′-methyl-biphenyl-3-carboxylic acid methyl ester a yellow solid (293 mg, 74.6%).

Workup

  1. customAfter removing the excess HOAc
  2. dissolutionthe residue was dissolved in EtOAc
  3. washwashed with saturated aqueous NaHCO3
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography (ISCO™)

Sources & evidence

ORD record
ord-abefdd1cc0ce4aa28665be7a8e1bda21
Source dataset
uspto-grants-2013_05
Patent number
US08440708B2

Reaction notes

Loading…