Trifluoroacetic acid → HCID 66814793, compound

HRID 1097581Notes

Reaction equation

HRID 1097581 reaction equation
FC(F)(F)C(O)=O.Br.[NH2:9][C:10]1[N:11]([CH2:42][CH2:43][CH2:44][NH:45]C(=O)OC(C)(C)C)[C:12]2[C:21]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[N:15]=[C:14]([N:22](CC3C=CC(OC)=CC=3)CC3C=CC(OC)=CC=3)[C:13]=2[N:41]=1>>[NH2:45][CH2:44][CH2:43][CH2:42][N:11]1[C:12]2[C:21]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[N:15]=[C:14]([NH2:22])[C:13]=2[N:41]=[C:10]1[NH2:9]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66814296HCID 66814296, compound

Product 1

HCID 66814793HCID 66814793, compoundYield 20.1%

Conditions

Temperature
50 °C

Procedure

Trifluoroacetic acid (28.15 mL, 365.5 mmol) was added to tert-butyl 3-{2-amino-4-[bis(4-methoxybenzyl)amino]-1H-imidazo[4,5-c]quinolin-1-yl}propylcarbamate hydrobromide (8.3 g), and the reaction was heated at 50° C. for four hours, allowed to cool to ambient temperature, and stirred at ambient temperature for three days. The volatiles were removed under reduced pressure. The residue was purified by automated flash chromagraphy (silica cartridge, eluting with aqueous ammonium hydroxide:methanol:dichloromethane in a gradient from 0.3:4.8:95 to 2.5:47.5:50) to provide 630 mg of 1-(3-aminopropyl)-1H-imidazo[4,5-c]quinoline-2,4-diamine.

Workup

  1. temperatureto cool to ambient temperature
  2. customThe volatiles were removed under reduced pressure
  3. customThe residue was purified by automated flash chromagraphy (silica cartridge
  4. washeluting with aqueous ammonium hydroxide

Sources & evidence

ORD record
ord-2dc44a0112144268acbbee599a8f242e
Source dataset
uspto-grants-2012_03
Patent number
US08143270B2

Reaction notes

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