Trifluoroacetic acid → HCID 59397877, compound

HRID 39789Notes

Reaction equation

HRID 39789 reaction equation
[O:1]=[C:2]([NH:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=1)[CH2:3][N:4]([CH:12]1[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][N:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[N:23]=[CH:22][C:21]2=[O:30])[CH2:14][CH2:13]1)C(=O)OC(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[O:30]=[C:21]1[CH:22]=[N:23][C:24]2[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:20]1[CH2:19][CH2:18][N:15]1[CH2:16][CH2:17][CH:12]([NH:4][CH2:3][C:2]([NH:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=2)=[O:1])[CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59398373tert-butyl (2-oxo-2-(pyridin-2-ylamino)ethyl)(1-(2-(2-oxoquinoxalin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate

Product 1

HCID 59397877HCID 59397877, compoundYield 95.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 3 mL of a dichloromethane solution containing 0.26 g of tert-butyl (2-oxo-2-(pyridin-2-ylamino)ethyl)(1-(2-(2-oxoquinoxalin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate, 3 mL of trifluoroacetic acid was added and stirred at room temperature for 1 hour. The solvent was removed under reduced pressure, chloroform and water were added, and adjusted to pH 11 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 sequentially with water and aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to give 0.20 g of N2-(1-(2-(2-oxoquinoxalin-1(2H)-yl)ethyl)piperidin-4-yl)-N-(pyridin-2-yl)glycinamide 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 sequentially with water and 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-12a73f028445491ca592ed0c9f0f022c
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Reaction notes

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