Ammonia → HCID 57515518, Verbindung

HRID 1469307Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1469307
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

Komponenten

4

Edukt 2

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

Produkt 1

HCID 57515518HCID 57515518, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-525bdbd4d7954904bb03369fae65d1dd
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09006264B2

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