Ammonia → HCID 57550543, compound

HRID 1097592Notes

Reaction equation

HRID 1097592 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 86626298HCID 86626298, compound

Product 1

HCID 57550543HCID 57550543, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Chloro-1-[(1S)-1-phenylethyl]-1H-imidazo[4,5-c]quinolin-2-amine hydrobromide (4.0 g, 12 mmol) was treated with ammonia (65 mL of a 7 N solution in methanol) according to the method in Part D of Example 44. The crude product was purified twice by automated flash chromatography (silica cartridge, eluting with aqueous ammonium hydroxide:methanol:dichloromethane in a gradient from 0:0:100 to 0.2:3.8:96). The chromatographed product was washed with diethyl ether several times and dried in a vacuum oven to provide 285 mg of 1-[(1S)-1-phenylethyl]-1H-imidazo[4,5-c]quinoline-2,4-diamine as a brown solid, mp 135-140° C.

Workup

  1. customThe crude product was purified twice by automated flash chromatography (silica cartridge
  2. washeluting with aqueous ammonium hydroxide
  3. washThe chromatographed product was washed with diethyl ether several times
  4. customdried in a vacuum oven

Sources & evidence

ORD record
ord-b7cdd1f455f142b6852b2df2fddad8b1
Source dataset
uspto-grants-2012_03
Patent number
US08143270B2

Reaction notes

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