Dimethylformamide dimethyl acetal → HCID 57770712, compound

HRID 2092626Notes

Reaction equation

HRID 2092626 reaction equation
[OH:1][CH:2]([CH3:6])[C:3]([NH2:5])=O.[CH3:7]OC(OC)N(C)C.[CH3:15][O:16][C:17]([C:19]1[CH:20]=[C:21]([C:27]2[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=2)[CH:22]=[C:23]([NH:25][NH2:26])[CH:24]=1)=[O:18]>COCCOC.CC(O)=O>[CH3:15][O:16][C:17]([C:19]1[CH:20]=[C:21]([C:27]2[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=2)[CH:22]=[C:23]([N:25]2[C:3]([CH:2]([OH:1])[CH3:6])=[N:5][CH:7]=[N:26]2)[CH:24]=1)=[O:18]

Participants

6

Reactant 3

HCID 78373Dimethylformamide dimethyl acetalHCID 94220LactamideHCID 57770761HCID 57770761, compound

Product 1

HCID 57770712HCID 57770712, compoundYield 29.76%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-hydroxy-propionamide (1.0 g, 11.2 mmol) and N,N-dimethylformamide dimethyl acetal (1.06 g, 8.96 mmol) in dimethyl glycol (6 mL) was heated to 80° C. for two hours, then cooled to room temperature. T mixture was added to a solution of 5-hydrazino-4′-methyl-biphenyl-3-carboxylic acid methyl ester (1.2 g, 4.1 mmol) in HOAc (5 mL), and the mixture was heated to 80° C. for another two hours. The reaction mixture was cooled and volatiles were removed under reduced pressure. 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 to afford 5-[5-(1-hydroxy-ethyl)-[1,2,4]triazol-1-yl]-4′-methyl-biphenyl-3-carboxylic acid methyl ester as a white solid (410 mg, 29.76%).

Workup

  1. temperaturecooled to room temperature
  2. temperaturethe mixture was heated to 80° C. for another two hours
  3. temperatureThe reaction mixture was cooled
  4. customvolatiles were removed under reduced pressure
  5. dissolutionThe residue was dissolved in EtOAc
  6. washwashed with saturated aqueous NaHCO3
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-3f4bd631b4174e56ac08a185f65268aa
Source dataset
uspto-grants-2013_05
Patent number
US08440708B2

Reaction notes

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