Trifluoroacetic acid → HCID 15985442, compound

HRID 2193133Notes

Reaction equation

HRID 2193133 reaction equation
C(OC(=O)[N:7]([CH2:30][C:31]1[CH:40]=[CH:39][C:34]2[O:35][CH2:36][CH2:37][O:38][C:33]=2[CH:32]=1)[CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][N:16]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([O:26][CH3:27])[CH:24]=3)[C:19]([CH3:28])=[CH:18][C:17]2=[O:29])[CH2:10][CH2:9]1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[O:35]1[C:34]2[CH:39]=[CH:40][C:31]([CH2:30][NH:7][CH:8]3[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][N:16]4[C:25]5[C:20](=[CH:21][CH:22]=[C:23]([O:26][CH3:27])[CH:24]=5)[C:19]([CH3:28])=[CH:18][C:17]4=[O:29])[CH2:10][CH2:9]3)=[CH:32][C:33]=2[O:38][CH2:37][CH2:36]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59398181HCID 59398181, compound

Product 1

HCID 15985442HCID 15985442, compoundYield 76.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 2 mL of a dichloromethane solution containing 95 mg of tert-butyl(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate, 2 mL of trifluoroacetic acid was added and stirred for 3 hours. The solvent was removed under reduced pressure, and aqueous saturated sodium hydrogen carbonate solution and ethyl acetate were added. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and extracts were combined, washed with aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [eluent; chloroform:methanol=9:1] to give 60 mg of 1-(2-(4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-7-methoxy-4-methylquinolin-2(1H)-one as a white solid.

Workup

  1. additionwas added
  2. customThe solvent was removed under reduced pressure, and aqueous saturated sodium hydrogen carbonate solution and ethyl acetate
  3. additionwere added
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. washwashed with aqueous saturated sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was removed under reduced pressure
  9. customThe residue thus obtained
  10. customwas purified by silica gel column chromatography [eluent; chloroform:methanol=9:1]

Sources & evidence

ORD record
ord-f1df98636ee141098d24c7ca70a79684
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Reaction notes

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