Sodium Methoxide → HCID 178440342, compound

HRID 714684Notes

Reaction equation

HRID 714684 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH:13]3[CH2:15][CH2:14]3)[C:11](=[O:16])[N:10]([CH2:17][C:18]([NH:20][NH2:21])=O)[N:9]=2)=[CH:4][CH:3]=1.Cl.[F:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[C:30]([CH3:35])([CH3:34])[C:31](=N)[NH2:32].C[O-].[Na+]>CN(C=O)C.CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH:13]3[CH2:15][CH2:14]3)[C:11](=[O:16])[N:10]([CH2:17][C:18]3[NH:32][C:31]([C:30]([C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=4[F:23])([CH3:35])[CH3:34])=[N:21][N:20]=3)[N:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 10942334Sodium MethoxideHCID 673967312-(2-Fluorophenyl)-2-methylpropaneimidamide hydrochlorideHCID 674061412-[3-(4-Chlorophenyl)-4-cyclopropyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]acetohydrazide

Product 1

HCID 178440342HCID 178440342, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

60 mg (0.20 mmol) of the compound from Example 21A were dissolved in 1 ml of DMF, and 63 mg (0.29 mmol) of 2-(2-fluorophenyl)-2-methylpropaneimidamide hydrochloride and 17 mg (0.31 mmol) of sodium methoxide were added. The suspension was stirred at 150° C. for 8 h. The reaction was then brought to completion by 45 min of stirring in a microwave reactor at 200° C. The suspension was diluted with about 1 ml of methanol and filtered, and the filtrate was purified by preparative HPLC [Method 19]. This gave 13 mg (15% of theory) of the title compound.

Workup

  1. waitThe reaction was then brought to completion by 45 min
  2. stirringof stirring in a microwave reactor at 200° C
  3. filtrationfiltered
  4. customthe filtrate was purified by preparative HPLC [Method 19]

Sources & evidence

ORD record
ord-fa4c50d5bee14c8d93a7e82dc29c60b5
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

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