Ammonia → HCID 57515518, compound

HRID 44766Notes

Reaction equation

HRID 44766 reaction equation
Cl[C:2]1[C:11]2[N:12]=[C:13]([CH2:21][CH2:22][CH3:23])[N:14]([CH2:15][C:16]3([OH:20])[CH2:19][CH2:18][CH2:17]3)[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.[NH3:24]>CO>[NH2:24][C:2]1[C:11]2[N:12]=[C:13]([CH2:21][CH2:22][CH3:23])[N:14]([CH2:15][C:16]3([OH:20])[CH2:19][CH2:18][CH2:17]3)[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 575155191-[(4-Chloro-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)methyl]cyclobutanol

Product 1

HCID 57515518HCID 57515518, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
150 °C

Procedure

1-[(4-Chloro-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)methyl]cyclobutanol (1.56 g) was combined with a solution of ammonia in methanol (23 mL). The mixture was heated at 150° C. in a pressure vessel for 2 days. A portion of the solvent was removed under vacuum and then the mixture was diluted with additional methanol. A solid was isolated by filtration, washed with methanol, triturated with acetonitrile, and then dried. The material was suspended in water (70 mL). Concentrated hydrochloric acid (1.4 mL) was added and the mixture was heated at 90° C. for 30 minutes. The hot solution was neutralized with solid sodium bicarbonate. The solution was allowed to cool to ambient temperature. A precipitate was isolated by filtration, washed well with water, and then dried to provide 1-[(4-amino-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)methyl]cyclobutanol as a white powder, mp 228.0-229.0° C. Anal. Calcd for C18H22N4O C, 69.65; H, 7.14; N, 18.05. Found: C, 69.36; H, 7.24; N, 18.03.

Workup

  1. customA portion of the solvent was removed under vacuum
  2. additionthe mixture was diluted with additional methanol
  3. customA solid was isolated by filtration
  4. washwashed with methanol
  5. customtriturated with acetonitrile
  6. customdried
  7. additionConcentrated hydrochloric acid (1.4 mL) was added
  8. temperaturethe mixture was heated at 90° C. for 30 minutes
  9. temperatureto cool to ambient temperature
  10. customA precipitate was isolated by filtration
  11. washwashed well with water
  12. customdried

Sources & evidence

ORD record
ord-bada755ca2b44d0ab26b78ebdf22c0de
Source dataset
uspto-grants-2013_09
Patent number
US08541438B2

Reaction notes

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