Trifluoroacetic acid → HCID 87250583, compound

HRID 599400Notes

Reaction equation

HRID 599400 reaction equation
FC(F)(F)C(O)=O.C(OC(=O)[NH:14][CH2:15][CH2:16][CH2:17][N:18]1[C:30]2[C:29]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[N:23]=[C:22]([NH2:31])[C:21]=2[N:20]=[C:19]1[CH2:32][O:33][N:34]=[C:35]([CH3:37])[CH3:36])(C)(C)C>ClCCl>[NH2:31][C:22]1[C:21]2[N:20]=[C:19]([CH2:32][O:33][N:34]=[C:35]([CH3:37])[CH3:36])[N:18]([CH2:17][CH2:16][CH2:15][NH2:14])[C:30]=2[C:29]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[N:23]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 131728724HCID 131728724, compound

Product 1

HCID 87250583HCID 87250583, compoundYield 243.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (7 mL) was added to a suspension of tert-butyl[3-(4-amino-2-isopropylideneaminoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)propyl]carbamate (4.12 g) in dichloromethane (70 mL). The reaction became homogeneous and was stirred at ambient temperature for 2.5 hours. More trifluoroacetic acid (10 mL) was added and the reaction was stirred for another hour. The reaction mixture was concentrated under reduced pressure and placed under high vacuum overnight to provide 7.68 g of propan-2-one O-{[4-amino-1-(3-aminopropyl)-1H-imidazo[4,5-c]quinolin-2-yl]methyl}oxime a white solid. Based on the weight this material was assumed to contain 5 equivalents of trifluoroacetic acid.

Workup

  1. stirringthe reaction was stirred for another hour
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customplaced under high vacuum overnight

Sources & evidence

ORD record
ord-4cbf13a285d44186ab3764ef8d3780ff
Source dataset
uspto-grants-2011_03
Patent number
US07897767B2

Reaction notes

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