Hydrogen chloride-ethyl acetate → HCID 68923643, compound

HRID 385638Notes

Reaction equation

HRID 385638 reaction equation
O1C2C=CC(CO[C:13](=O)[NH:14][CH:15]3[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][N:23]4[C:32]5[C:27](=[CH:28][CH:29]=[C:30]([O:33][CH3:34])[N:31]=5)[CH:26]=[CH:25][C:24]4=[O:35])[CH2:17][CH2:16]3)=CC=2OCC1.[ClH:37].[C:38]([O:41][CH2:42][CH3:43])(=O)[CH3:39]>>[ClH:37].[O:41]1[C:38]2[CH:39]=[CH:27][C:28]([CH2:13][NH:14][CH:15]3[CH2:16][CH2:17][N:18]([CH2:21][CH2:22][N:23]4[C:32]5[C:27](=[CH:28][CH:29]=[C:30]([O:33][CH3:34])[N:31]=5)[CH:26]=[CH:25][C:24]4=[O:35])[CH2:19][CH2:20]3)=[CH:29][C:30]=2[O:33][CH2:43][CH2:42]1

Participants

3

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 131729802HCID 131729802, compound

Product 1

HCID 68923643HCID 68923643, compound

Procedure

To 0.50 g of tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl(1-(2-(7-methoxy-2-oxo-1,8-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate, 15 mL of a 4 mol/L hydrogen chloride/ethyl acetate solution was added, and the mixture was stirred at room temperature for 43 hours. The solvent was distilled off under reduced pressure, methanol was added to the resultant residue, and the solvent was distilled off under reduced pressure. Then, ethyl acetate was added to the resultant residue, and the solid was filtered off to obtain 0.41 g of 1-(2-(4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-7-methoxy-1,8-naphthyridin-2(1H)-one hydrochloride as a light yellow solid.

Workup

  1. distillationThe solvent was distilled off under reduced pressure, methanol
  2. additionwas added to the resultant residue
  3. distillationthe solvent was distilled off under reduced pressure
  4. additionThen, ethyl acetate was added to the resultant residue
  5. filtrationthe solid was filtered off

Sources & evidence

ORD record
ord-6c2d8e535d4042579edd3b91aa380f97
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

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