Trifluoroacetic acid → HCID 67539295, compound

HRID 39947Notes

Reaction equation

HRID 39947 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][N:12]([CH:20]3[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][N:28]4[C:37]5[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=5)[C:31]([C:38]5[CH:43]=[CH:42][N:41]=[CH:40][CH:39]=5)=[CH:30][C:29]4=[O:44])[CH2:22][CH2:21]3)C(=O)OC(C)(C)C)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+].[ClH:57].C(OCC)(=O)C>C(Cl)(Cl)Cl>[ClH:57].[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][NH:12][CH:20]3[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][N:28]4[C:37]5[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=5)[C:31]([C:38]5[CH:39]=[CH:40][N:41]=[CH:42][CH:43]=5)=[CH:30][C:29]4=[O:44])[CH2:22][CH2:21]3)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 21866389Hydrogen chloride-ethyl acetateHCID 59397987HCID 59397987, compound

Product 1

HCID 67539295HCID 67539295, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To 1 mL of a chloroform solution containing 42 mg of tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(2-oxo-4-(pyridin-4-yl)quinolin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate, 1 mL of trifluoroacetic acid was added at room temperature and stirred for 3.5 hours, thereafter the solvent was removed under reduced pressure. To the residue thus obtained, chloroform and aqueous saturated sodium hydrogen carbonate solution were added, 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 the residue thus obtained, 1 mL of 4 mol/L hydrogen chloride/ethyl acetate was added, the resulting solid was filtered to give 21 mg of (1-(2-(4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-4-(pyridin-4-yl)quinolin-2(1H)-one hydrochloride as a pale yellow solid.

Workup

  1. additionwas added at room temperature
  2. customthe solvent was removed under reduced pressure
  3. customTo the residue thus obtained
  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
  9. customTo the residue thus obtained
  10. filtrationthe resulting solid was filtered

Sources & evidence

ORD record
ord-7c72d1841ab2403792b3786ac6469ae6
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Reaction notes

Loading…