Trifluoroacetic acid → N-(pyridin-2-yl)-N2-(1-(2-(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)glycinamide

HRID 2193146Notes

Reaction equation

HRID 2193146 reaction equation
C(OC(=O)[N:7]([CH:18]1[CH2:23][CH2:22][N:21]([CH2:24][CH2:25][N:26]2[C:35]3[C:30](=[CH:31][CH:32]=[C:33]([O:36][CH3:37])[CH:34]=3)[C:29]([CH3:38])=[CH:28][C:27]2=[O:39])[CH2:20][CH2:19]1)[CH2:8][C:9](=[O:17])[NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[N:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[NH:10][C:9](=[O:17])[CH2:8][NH:7][CH:18]1[CH2:23][CH2:22][N:21]([CH2:24][CH2:25][N:26]2[C:35]3[C:30](=[CH:31][CH:32]=[C:33]([O:36][CH3:37])[CH:34]=3)[C:29]([CH3:38])=[CH:28][C:27]2=[O:39])[CH2:20][CH2:19]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59398207tert-butyl(1-(2-(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)(2-oxo-2-(pyridin-2-ylamino)ethyl)carbamate

Product 1

HCID 15985507N-(pyridin-2-yl)-N2-(1-(2-(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)glycinamideYield 92.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 5 mL of a dichloromethane solution containing 0.11 g of tert-butyl(1-(2-(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)(2-oxo-2-(pyridin-2-ylamino)ethyl)carbamate, 5 mL of trifluoroacetic acid was added and stirred at room temperature for 30 min. The solvent was removed under reduced pressure, chloroform and water were added, and adjusted to pH 13 with 20% aqueous sodium hydroxide solution under ice-cooling. The organic layer was separated, and the aqueous layer was extracted with chloroform. 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 to give 83 mg of N- (pyridin-2-yl)-N2-(1-(2-(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)glycinamide as a light brown foam.

Workup

  1. additionwas added
  2. customThe solvent was removed under reduced pressure, chloroform and water
  3. additionwere added
  4. temperaturecooling
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted with chloroform
  7. washwashed with aqueous saturated sodium chloride solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-3d1906686dbb4ac2baf9a3f44aec8fb7
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Reaction notes

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