Hydrogen chloride-ethyl acetate → HCID 57815413, compound

HRID 385691Notes

Reaction equation

HRID 385691 reaction equation
C(OC([NH:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][C:15](=[O:46])[N:16]2[CH2:19][CH2:20][N:21]2[CH2:26][CH2:25][CH:24]([N:27]([CH2:35][C:36]3[N:41]=[CH:40][C:39]4[O:42][CH2:43][CH2:44][O:45][C:38]=4[CH:37]=3)C(=O)OC(C)(C)C)[CH2:23][CH2:22]2)=[N:11][CH:10]=1)=O)(C)(C)C.Cl.C(OCC)(=O)C>CO>[NH2:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][C:15](=[O:46])[N:16]2[CH2:19][CH2:20][N:21]2[CH2:22][CH2:23][CH:24]([NH:27][CH2:35][C:36]3[N:41]=[CH:40][C:39]4[O:42][CH2:43][CH2:44][O:45][C:38]=4[CH:37]=3)[CH2:25][CH2:26]2)=[N:11][CH:10]=1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 57815323HCID 57815323, compound

Product 1

HCID 57815413HCID 57815413, compoundYield 68.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 0.66 g of tert-butyl (1-(2-(7-((tert-butoxycarbonyl)amino)-2-oxo-1,5-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)(2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-ylmethyl)carbamate in 8 mL of methanol, 8 mL of a 4 mol/L hydrogen chloride/ethyl acetate solution was added at room temperature, the mixture was stirred for 18 hours, and then the solid was filtered off. Subsequently, the solid was suspended in 3 mL of chloroform, thereto was added 6 mL of trifluoroacetic acid at room temperature, the mixture was stirred for 2 hours, and the solvent was then distilled off under reduced pressure. The residue was charged with chloroform and water and adjusted to pH 9 with a 2 mol/L aqueous sodium hydroxide solution, and the organic layer was separated. The aqueous layer was extracted with chloroform three times and combined with the organic layer, the resultant solution was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 0.31 g of 7-amino-1-(2-(4-((2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-ylmethyl)amino)piperidin-1-yl)ethyl)-1,5-naphthyridin-2(1H)-one as a white foam.

Workup

  1. filtrationthe solid was filtered off
  2. additionwas added 6 mL of trifluoroacetic acid at room temperature
  3. stirringthe mixture was stirred for 2 hours
  4. distillationthe solvent was then distilled off under reduced pressure
  5. additionThe residue was charged with chloroform and water
  6. customthe organic layer was separated
  7. extractionThe aqueous layer was extracted with chloroform three times
  8. washthe resultant solution was washed with a saturated aqueous sodium chloride solution
  9. dry with materialdried over anhydrous magnesium sulfate
  10. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-b1f9039278ff49808d123f80bd73742c
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

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