Ammonia → HCID 57550542, compound

HRID 1097585Notes

Reaction equation

HRID 1097585 reaction equation
Br.Cl[C:3]1[C:12]2[N:13]=[C:14]([NH2:21])[N:15]([CH2:16][C:17]([F:20])([CH3:19])[CH3:18])[C:11]=2[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[N:4]=1.[NH3:22]>CO>[F:20][C:17]([CH3:19])([CH3:18])[CH2:16][N:15]1[C:11]2[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]=[C:3]([NH2:22])[C:12]=2[N:13]=[C:14]1[NH2:21]

Participants

4

Reactant 2

HCID 222Ammonia2×HCID 86626291HCID 86626291, compound

Product 1

HCID 57550542HCID 57550542, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
150 °C

Procedure

Crude 4-chloro-1-(2-fluoro-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-2-amine hydrobromide (1.14 g) and ammonia (approximately 100 mL of a 7 N solution in methanol) were added to a pressure vessel, which was sealed and heated at 150° C. for five days. Additional ammonia in methanol was added after three days and again after four days. When the reaction was complete, the volatiles were removed under reduced pressure, and the residue was combined with material from another run. The crude product was purified by automated flash chromatography (silica cartridge, eluting with aqueous ammonium hydroxide:methanol:dichloromethane in a gradient from 0:0:100 to 1:14:85) to provide 270 mg of 1-(2-fluoro-2-methylpropyl)-1H-imidazo[4,5-c]quinoline-2,4-diamine as a light tan solid, mp 251° C.

Workup

  1. customwhich was sealed
  2. customthe volatiles were removed under reduced pressure
  3. customThe crude product was purified by automated flash chromatography (silica cartridge
  4. washeluting with aqueous ammonium hydroxide

Sources & evidence

ORD record
ord-aca90b36ef944dd58e5b12262969a5ed
Source dataset
uspto-grants-2012_03
Patent number
US08143270B2

Reaction notes

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