Trifluoroacetic acid → HCID 68810511, compound

HRID 656908Notes

Reaction equation

HRID 656908 reaction equation
[CH2:1]([C:3]1[C:4]([F:30])=[CH:5][N:6]=[C:7]2[C:12]=1[N:11]([CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][CH:18]([NH:21]C(=O)OC(C)(C)C)[CH2:17][CH2:16]1)[C:10](=[O:29])[CH:9]=[CH:8]2)[CH3:2].C(O)(C(F)(F)F)=O.CC[NH+](CC)CC.CC[NH+](CC)CC.C([O-])([O-])=O>C(Cl)Cl.CO>[NH2:21][CH:18]1[CH2:17][CH2:16][N:15]([CH2:14][CH2:13][N:11]2[C:12]3[C:7](=[N:6][CH:5]=[C:4]([F:30])[C:3]=3[CH2:1][CH3:2])[CH:8]=[CH:9][C:10]2=[O:29])[CH2:20][CH2:19]1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 15264167Carbonic acid--N,N-diethylethanamine (1/2)HCID 86635315HCID 86635315, compound

Product 1

HCID 68810511HCID 68810511, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1,1-dimethylethyl {1-[2-(8-ethyl-7-fluoro-2-oxo-1,5-naphthyridin-1(2H)-yl)ethyl]-4-piperidinyl}carbamate (0.234 g, 0.559 mmol) in DCM (2 ml) was added TFA (1 ml) and the reaction was allowed to stirred at rt for 1 h before evaporation of solvent. The residue was dissolved in 1:1 DCM and MeOH (2 ml) and then treated with MP-Carbonate resin until the pH reached 8. The reaction was then filtered, resin washed with MeOH and the filtrate was evaporated to dryness to give a yellow oil (0.176 g, 99%).

Workup

  1. filtrationThe reaction was then filtered
  2. washresin washed with MeOH
  3. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-f57dc363b48e40e28920f5da53abe0a4
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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