Trifluoroacetic acid → HCID 86627651, compound

HRID 1907941Notes

Reaction equation

HRID 1907941 reaction equation
FC(F)(F)C(O)=O.C(OC(=O)[NH:14][CH2:15][CH2:16][N:17]1[C:29]2[C:28]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[N:22]=[C:21]([NH2:30])[C:20]=2[N:19]=[C:18]1[CH2:31][O:32][N:33]=[C:34]([CH3:36])[CH3:35])(C)(C)C>ClCCl>[NH2:30][C:21]1[C:20]2[N:19]=[C:18]([CH2:31][O:32][N:33]=[C:34]([CH3:36])[CH3:35])[N:17]([CH2:16][CH2:15][NH2:14])[C:29]=2[C:28]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[N:22]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 86627652HCID 86627652, compound

Product 1

HCID 86627651HCID 86627651, compoundYield 274.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (10 mL) was added to a suspension of tert-butyl[2-(4-amino-2-isopropylideneaminooxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]carbamate (4.8 g) in dichloromethane (100 mL). The reaction became homogeneous and was stirred at ambient temperature. At 2.5 hours and 3.5 hours more trifluoroacetic acid (10 mL and 5 mL respectively) was added. After a total reaction time of 4 hours the reaction mixture was concentrated under reduced pressure. The residue was azeotroped with toluene (×3) and then placed under high vacuum overnight to provide 9.97 g of propan-2-one O-{[4-amino-1-(2-aminoethyl)-1H-imidazo[4,5-c]quinolin-2-yl]methyl}oxime as a yellow solid. Based on the weight this material was assumed to contain 5 equivalents of trifluoroacetic acid.

Workup

  1. concentrationAfter a total reaction time of 4 hours the reaction mixture was concentrated under reduced pressure
  2. customThe residue was azeotroped with toluene (×3)
  3. customplaced under high vacuum overnight

Sources & evidence

ORD record
ord-2bb5d8ebc9bc4e35b8171a534b842b9d
Source dataset
uspto-grants-2013_12
Patent number
US08598192B2

Reaction notes

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