Ammonia → N-[2-(2,4-diamino-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethyl]methanesulfonamide

HRID 1097557Notes

Reaction equation

Br.[NH2:2][C:3]1[N:4]([CH2:17][C:18]([NH:21][S:22]([CH3:25])(=[O:24])=[O:23])([CH3:20])[CH3:19])[C:5]2[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:8]=[C:7](Cl)[C:6]=2[N:16]=1.[NH3:26]>CO>[NH2:2][C:3]1[N:4]([CH2:17][C:18]([NH:21][S:22]([CH3:25])(=[O:24])=[O:23])([CH3:20])[CH3:19])[C:5]2[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:8]=[C:7]([NH2:26])[C:6]=2[N:16]=1

Participants

Conditions

Temperature: 150 °C

Procedure

Crude N-[2-(2-amino-4-chloro-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethyl]methanesulfonamide hydrobromide (0.400 g) and ammonia (25 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. The resulting solution was concentrated under reduced pressure, and the residue was purified by flash chromatography on silica gel (eluting with 2-6% methanol in dichloromethane with 1% ammonium hydroxide added.) A portion of the product was recrystallized from acetonitrile and a small amount of methanol, isolated by filtration, and washed with diethyl ether to provide 39 mg of N-[2-(2,4-diamino-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethyl]methanesulfonamide as brown needles, mp >230° C.

Workup

customwhich was sealed
concentrationThe resulting solution was concentrated under reduced pressure
customthe residue was purified by flash chromatography on silica gel (eluting with 2-6% methanol in dichloromethane with 1% ammonium hydroxide added.) A portion of the product
customwas recrystallized from acetonitrile
customa small amount of methanol, isolated by filtration
washwashed with diethyl ether

Sources & evidence

ORD record: ord-8b8d9f405ad246f1a6d6b7c78cc540f0
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08143270B2

Reaction notes

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