Potassium Carbonate → HCID 178446281, compound

HRID 600587Notes

Reaction equation

HRID 600587 reaction equation
[CH2:1]([NH:6][C:7]1[N:8]=[CH:9][NH:10][C:11]=1[C:12]#[N:13])[CH2:2][CH2:3][CH2:4][CH3:5].[C:14]([NH:17][NH2:18])(=O)[CH3:15].C(=O)([O-])[O-].[K+].[K+]>C(O)CCC.O>[CH3:15][C:14]1[N:13]=[C:12]([C:11]2[NH:10][CH:9]=[N:8][C:7]=2[NH:6][CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[NH:18][N:17]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 14039AcetohydrazideHCID 451205654-(pentylamino)-1H-imidazole-5-carbonitrile

Product 1

HCID 178446281HCID 178446281, compoundYield 10%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 962WaterSolvent

Conditions

Temperature
165 °C

Procedure

To the mixture of 4-(pentylamino)-1H-imidazole-5-carbonitrile (0.40 g, 2 mmol), acetic acid, hydrazide (0.33 g, 4.5 mmol) in 1-butanol (10 mL) was added potassium carbonate (0.10 g, 0.72 mmol). The mixture was sealed and stirred at 165° C. for 14 hours. The reaction mixture was diluted with water and extracted with ethyl acetate three times. The combined organic layers were dried with sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by preparative LCMS (method A) to yield the desired product (45 mg, 10% yield). LCMS calculated for C11H19N6(M+H): 235.2. found: 235.1.

Workup

  1. customThe mixture was sealed
  2. extractionextracted with ethyl acetate three times
  3. dry with materialThe combined organic layers were dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by preparative LCMS (method A)

Sources & evidence

ORD record
ord-4681e74ea04f4f0db06bdbd5b355703b
Source dataset
uspto-grants-2011_03
Patent number
US07902205B2

Reaction notes

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