Ammonia → HCID 57550531, compound

HRID 1097567Notes

Reaction equation

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

Participants

Conditions

Temperature: 150 °C

Procedure

1-[4-Chloro-2-(ethylamino)-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol (2.49 g, 7.81 mmol) and ammonia (70 mL of a 7 N solution in methanol) were added to a high-pressure vessel, which was sealed and heated overnight in an oven at 150° C. An analysis by HPLC indicated the presence of starting material, and additional ammonia in methanol (10 mL) was added. The reaction was heated for four hours at 150° C. and cooled to ambient temperature. The solvent was removed under reduced pressure, and the residue was purified by flash chromatography on silica gel (eluting with 2-2.5% methanol in dichloromethane with 1% ammonium hydroxide added.) A portion of the product was recrystallized from methanol, isolated by filtration, and washed with cold methanol to provide 496 mg of 1-[4-amino-2-(ethylamino)-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol as white needles, mp 233-235° C.

Workup

customwhich was sealed
additionwas added
temperatureThe reaction was heated for four hours at 150° C.
temperaturecooled to ambient temperature
customThe solvent was removed under reduced pressure
customthe residue was purified by flash chromatography on silica gel (eluting with 2-2.5% methanol in dichloromethane with 1% ammonium hydroxide added.) A portion of the product
customwas recrystallized from methanol
customisolated by filtration
washwashed with cold methanol

Sources & evidence

ORD record: ord-8f1e09f195ed42818fdb03ac8a1e6935
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08143270B2

Reaction notes

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