Trifluoroacetic acid → HCID 15985573, compound

HRID 2193148Notes

Reaction equation

HRID 2193148 reaction equation
C(OC(=O)[N:7]([CH:19]1[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][N:27]2[C:36]3[C:31](=[C:32](Br)[CH:33]=[C:34]([O:37][CH3:38])[CH:35]=3)[CH:30]=[CH:29][C:28]2=[O:40])[CH2:21][CH2:20]1)[CH2:8][C:9]1[CH:18]=[CH:17][C:12]2[O:13][CH2:14][CH2:15][O:16][C:11]=2[CH:10]=1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[O:13]1[C:12]2[CH:17]=[CH:18][C:9]([CH2:8][NH:7][CH:19]3[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][N:27]4[C:36]5[C:31](=[CH:32][CH:33]=[C:34]([O:37][CH3:38])[CH:35]=5)[CH:30]=[CH:29][C:28]4=[O:40])[CH2:21][CH2:20]3)=[CH:10][C:11]=2[O:16][CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59397948tert-butyl (1-(2-(5-bromo-7-methoxy-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)carbamate

Product 1

HCID 15985573HCID 15985573, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 2 mL of a dichloromethane solution containing 20 mg of tert-butyl(1-(2-(5-bromo-7-methoxy-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4- yl)(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)carbamate, 1 mL of trifluoroacetic acid was added and stirred at room temperature for 2 hours. The solvent was removed under reduced pressure, chloroform and water were added, and adjusted to pH 13 with 20% aqueous sodium hydroxide solution. 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 16 mg of 5-bromo-1-(2-(4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl-7-methoxyquinolin-2(1H)-one as a light brown oil.

Workup

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

Sources & evidence

ORD record
ord-5a0a4795337140b680196ad8a255275d
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Reaction notes

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