Dimethylamine → HCID 57770831, compound

HRID 1669899Notes

Reaction equation

HRID 1669899 reaction equation
[C:1]([NH:6][NH2:7])(=O)[CH:2]([CH3:4])[CH3:3].CNC.[CH3:11][C:12]#N.[CH3:14][O:15][C:16]([C:18]1[CH:19]=[C:20]([C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=2)[CH:21]=[C:22]([NH2:24])[CH:23]=1)=[O:17]>C(O)(=O)C>[CH3:14][O:15][C:16]([C:18]1[CH:19]=[C:20]([C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=2)[CH:21]=[C:22]([N:24]2[C:11]([CH3:12])=[N:7][N:6]=[C:1]2[CH:2]([CH3:4])[CH3:3])[CH:23]=1)=[O:17]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 6342AcetonitrileHCID 192392-MethylpropanehydrazideHCID 57850917Methyl 5-amino-4'-methylbiphenyl-3-carboxylate

Product 1

HCID 57770831HCID 57770831, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

Isobutyric acid hydrazide (55 mg, 5.34 mmol) and 1,1-dimethoxy-ethyl)-dimethyl-amine (774 mg, 5.81 mmol) were added to 6 mL CH3CN and the mixture was heated to 50° C. and stirred for 30 minutes. 5-Amino-4′-methyl-biphenyl-3-carboxylic acid methyl ester (1.0 g, 4.15 mmol) was added, followed by 6 mL of acetic acid. The reaction mixture was heated to 120° C. and stirred for five hours, then cooled to room temperature. Solvent was removed under reduced pressure and the residue was purified via flash chromatography to give 400 mg (30%) of 5-(3-Isopropyl-5-methyl-[1,2,4]triazol-4-yl)-4′-methyl-biphenyl-3-carboxylic acid methyl ester as a white powder.

Workup

  1. temperatureThe reaction mixture was heated to 120° C.
  2. stirringstirred for five hours
  3. temperaturecooled to room temperature
  4. customSolvent was removed under reduced pressure
  5. customthe residue was purified via flash chromatography

Sources & evidence

ORD record
ord-8c5cdf33d28b48f9ab493db3622f4d5f
Source dataset
uspto-grants-2011_08
Patent number
US07989637B2

Reaction notes

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