Ammonia → HCID 57550530, compound

HRID 1097589Notes

Reaction equation

HRID 1097589 reaction equation
Br.Cl[C:3]1[C:12]2[N:13]=[C:14]([NH2:24])[N:15]([C@@H:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH3:17])[C:11]=2[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[N:4]=1.[NH3:25]>CO>[C:18]1([C@H:16]([N:15]2[C:11]3[C:10]4[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=4[N:4]=[C:3]([NH2:25])[C:12]=3[N:13]=[C:14]2[NH2:24])[CH3:17])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 86626295HCID 86626295, compound

Product 1

HCID 57550530HCID 57550530, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
135 °C

Procedure

4-Chloro-1-[(1R)-1-phenylethyl]-1H-imidazo[4,5-c]quinolin-2-amine hydrobromide (4.2 g, 13 mmol) and ammonia (65 mL of a 7 N solution in methanol) were added to a high-pressure vessel, which was sealed and heated in an oven at 135° C. overnight. The reaction mixture was concentrated under reduced pressure, and the residue was purified by automated flash chromatography (silica cartridge, eluting with aqueous ammonium hydroxide:methanol:dichloromethane in a gradient from 0:0:100 to 0.4:7.6:92). The chromatographed product was washed with diethyl ether to provide 362 mg of 1-[(1R)-1-phenylethyl]-1H-imidazo[4,5-c]quinoline-2,4-diamine as brown needles, mp 156-160° C.

Workup

  1. customwhich was sealed
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by automated flash chromatography (silica cartridge
  4. washeluting with aqueous ammonium hydroxide
  5. washThe chromatographed product was washed with diethyl ether

Sources & evidence

ORD record
ord-7268effb37fc495382a9bb816554db19
Source dataset
uspto-grants-2012_03
Patent number
US08143270B2

Reaction notes

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