Triethylamine → HCID 57557290, compound

HRID 81910Notes

Reaction equation

HRID 81910 reaction equation
C(N(CC)CC)C.[C:8](Cl)(=[O:12])[CH:9]([CH3:11])[CH3:10].[NH2:14][C:15]([CH3:36])([CH3:35])[CH2:16][N:17]1[C:29]2[C:28]3[N:27]=[CH:26][CH:25]=[CH:24][C:23]=3[N:22]=[C:21]([NH2:30])[C:20]=2[N:19]=[C:18]1[CH2:31][O:32][CH2:33][CH3:34]>ClCCl>[NH2:30][C:21]1[C:20]2[N:19]=[C:18]([CH2:31][O:32][CH2:33][CH3:34])[N:17]([CH2:16][C:15]([NH:14][C:8](=[O:12])[CH:9]([CH3:11])[CH3:10])([CH3:35])[CH3:36])[C:29]=2[C:28]2[N:27]=[CH:26][CH:25]=[CH:24][C:23]=2[N:22]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62325Isobutyryl chlorideHCID 68933946HCID 68933946, compound

Product 1

HCID 57557290HCID 57557290, compoundYield 60.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (556 μL, 4.00 mmol) and isobutyryl chloride (230 μL, 2.20 mmol) were added sequentially to a chilled (0° C.) solution of 1-(2-amino-2-methylpropyl)-2-ethoxymethyl-1H-imidazo[4,5-c][1,5]naphthyridin-4-amine (628 mg, 2.00 mmol) in dichloromethane (20 mL). The reaction mixture was allowed to warm slowly to ambient temperature overnight. The reaction mixture was quenched with aqueous saturated sodium bicarbonate and diluted with dichloromethane (50 mL). The organic layer was separated, washed sequentially with water and brine, dried over sodium sulfate, filtered, and then concentrated under reduced pressure to an amber foam. This material was dissolved in hot propyl acetate (10 mL) and then allowed to cool overnight. Hexanes were added and the now cloudy solution was heated until clear and then allowed stand until crystals formed. The solvent was removed by pipette. The crystals were rinsed with cold propyl acetate/hexanes and then dried under high vacuum at 70° C. to provide 464 mg of N-[2-(4-amino-2-ethoxymethyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)-1,1-dimethylethyl]-2-methylpropionamide as an off white crystalline solid, mp 154.5-155.5° C. Anal. calcd for C20H28N6O2: % C, 62.48; % H, 7.34; % N, 21.86. Found: % C, 62.14; % H, 7.62; % N, 21.71.

Workup

  1. customThe reaction mixture was quenched with aqueous saturated sodium bicarbonate
  2. additiondiluted with dichloromethane (50 mL)
  3. customThe organic layer was separated
  4. washwashed sequentially with water and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure to an amber foam
  8. dissolutionThis material was dissolved in hot propyl acetate (10 mL)
  9. temperatureto cool overnight
  10. additionHexanes were added
  11. temperaturethe now cloudy solution was heated until clear and
  12. customformed
  13. customThe solvent was removed by pipette
  14. washThe crystals were rinsed with cold propyl acetate/hexanes
  15. customdried under high vacuum at 70° C.

Sources & evidence

ORD record
ord-19dec32ddf1049adb51e765b4f6e4949
Source dataset
uspto-grants-2014_09
Patent number
US08846710B2

Reaction notes

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