Hydrogen chloride-ethyl acetate → HCID 24866870, compound

HRID 385628Notes

Reaction equation

HRID 385628 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][N:34]=[CH:35][CH:36]=5)[CH:31]=[CH:30][C:29]4=[O:38])[CH2:22][CH2:21]3)C(=O)OC(C)(C)C)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.[ClH:39].C(OCC)(=O)C>>[ClH:39].[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][N:34]=[CH:35][CH:36]=5)[CH:31]=[CH:30][C:29]4=[O:38])[CH2:22][CH2:21]3)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetate2×HCID 57815276tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(2-oxo-1,6-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate

Product 1

HCID 24866870HCID 24866870, compound

Procedure

To 0.15 g of tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(2-oxo-1,6-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate, 10 mL of a 4 mol/L hydrogen chloride/ethyl acetate solution was added, and the mixture was stirred at room temperature for 2 hours 30 minutes. Thereto was further added 5 mL of a 4 mol/L hydrogen chloride/ethyl acetate solution, the mixture was reacted at room temperature for 20 hours, and the solvent was distilled off under reduced pressure. The mixture was dissolved in 8 mL of 6 mol/L hydrochloric acid, and then the solvent was distilled off under reduced pressure. Ethanol was added to the resultant residue, and the solvent was distilled off under reduced pressure, and ethyl acetate was then added to the resultant residue, and the solid was filtered off to obtain 0.13 g of 1-(2-(4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-1,6-naphthyridin-2(1H)-one hydrochloride as a light yellow solid.

Workup

  1. customthe mixture was reacted at room temperature for 20 hours
  2. distillationthe solvent was distilled off under reduced pressure
  3. dissolutionThe mixture was dissolved in 8 mL of 6 mol/L hydrochloric acid
  4. distillationthe solvent was distilled off under reduced pressure
  5. additionEthanol was added to the resultant residue
  6. distillationthe solvent was distilled off under reduced pressure, and ethyl acetate
  7. additionwas then added to the resultant residue
  8. filtrationthe solid was filtered off

Sources & evidence

ORD record
ord-a5fc0686dc92473391f06a1b05b83fa9
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

Loading…