Pyridine → HCID 58500140, compound

HRID 1920277Notes

Reaction equation

HRID 1920277 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4](S(O)(=O)=O)=CC=1.[NH2:12][CH:13]([C:16]#[N:17])[C:14]#[N:15].N1C=CC=CC=1.C(OC)(OC)(OC)CCCC.[NH2:35][CH:36]([CH2:39][CH3:40])[CH2:37][CH3:38]>C(#N)C>[NH2:15][C:14]1[N:35]([CH:36]([CH2:39][CH3:40])[CH2:37][CH3:38])[C:4]([CH2:5][CH2:6][CH2:1][CH3:11])=[N:12][C:13]=1[C:16]#[N:17]

Participants

6

Reactant 4

HCID 1049PyridineHCID 120193-PentanamineHCID 83755Trimethyl orthovalerateHCID 563049Aminomalononitrile p-toluenesulphonate

Product 1

HCID 58500140HCID 58500140, compoundYield 112.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

Aminomalononitrile p-toluenesulfonate (1.00 g, 3.95 mmol), pyridine (0.32 mL, 3.95 mmol), and trimethyl orthovalerate (1.36 mL, 7.90 mmol) were combined in acetonitrile (16 mL), and the solution was heated at 85° C. for 1 hour. 3-Aminopentane (0.7 mL, 6 mmol) was added, and the reaction was heated for 1 hour and ten minutes and then allowed to cool to room temperature overnight. The solvent was removed under reduced pressure, and the resulting oil was partitioned between aqueous sodium bicarbonate and ethyl acetate. The ethyl acetate layer was separated and washed with aqueous sodium bicarbonate, water, and brine. The combined aqueous fractions were extracted with ethyl acetate, and the combined organic fractions were dried over sodium sulfate, filtered, and concentrated under reduced pressure to provide 1.04 g of crude 5-amino-2-butyl-1-(1-ethylpropyl)-1H-imidazole-4-carbonitrile as a brown oil. 1H-NMR (300 MHz, CDCl3) δ 3.90-3.78 (m, 1H), 3.71 (br s, 2H), 2.55 (m, 2H), 0.95 (t, J=7.3, 3H), 0.86 (t, J=7.4, 6H); MS (ESI) m/z (M+1)+235.

Workup

  1. temperaturethe reaction was heated for 1 hour and ten minutes
  2. temperatureto cool to room temperature overnight
  3. customThe solvent was removed under reduced pressure
  4. customthe resulting oil was partitioned between aqueous sodium bicarbonate and ethyl acetate
  5. customThe ethyl acetate layer was separated
  6. washwashed with aqueous sodium bicarbonate, water, and brine
  7. extractionThe combined aqueous fractions were extracted with ethyl acetate
  8. dry with materialthe combined organic fractions were dried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-454ff4a26caa4536bacd9eaea6de875b
Source dataset
uspto-grants-2012_05
Patent number
US08168802B2

Reaction notes

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