Hydrogen chloride-ethyl acetate → 1-(2-(3-(((2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-ylmethyl)amino)methyl)piperidin-1-yl)ethyl)-7-fluoro-1,5-naphthyridin-2(1H)-one hydrochloride

HRID 385665Notes

Reaction equation

HRID 385665 reaction equation
[O:1]1[C:10]2[CH:9]=[C:8]([CH2:11][NH:12][CH2:13][CH:14]3[CH2:19][CH2:18][CH2:17][N:16]([CH2:20][CH2:21][N:22]4[C:31]5[C:26](=[N:27][CH:28]=[C:29]([F:32])[CH:30]=5)[CH:25]=[CH:24][C:23]4=[O:33])[CH2:15]3)[N:7]=[CH:6][C:5]=2[O:4][CH2:3][CH2:2]1.[ClH:34].C(OCC)(=O)C>C(OCC)(=O)C>[ClH:34].[O:1]1[C:10]2[CH:9]=[C:8]([CH2:11][NH:12][CH2:13][CH:14]3[CH2:19][CH2:18][CH2:17][N:16]([CH2:20][CH2:21][N:22]4[C:31]5[C:26](=[N:27][CH:28]=[C:29]([F:32])[CH:30]=5)[CH:25]=[CH:24][C:23]4=[O:33])[CH2:15]3)[N:7]=[CH:6][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 578153161-(2-(3-(((2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-ylmethyl)amino)methyl)piperidin-1-yl)ethyl)-7-fluoro-1,5-naphthyridin-2(1H)-one

Product 1

HCID 689323101-(2-(3-(((2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-ylmethyl)amino)methyl)piperidin-1-yl)ethyl)-7-fluoro-1,5-naphthyridin-2(1H)-one hydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.14 g of 1-(2-(3-(((2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-ylmethyl)amino)methyl)piperidin-1-yl)ethyl)-7-fluoro-1,5-naphthyridin-2(1H)-one in 4 mL of ethyl acetate, 1 mL of a 4 mol/L hydrogen chloride/ethyl acetate solution was added, and the mixture was stirred at room temperature for 20 minutes. The solvent was distilled off under reduced pressure, diethyl ether was added to the resultant residue, and the solid was filtered off to obtain 0.10 g of 1-(2-(3-(((2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-ylmethyl)amino)methyl)piperidin-1-yl)ethyl)-7-fluoro-1,5-naphthyridin-2(1H)-one hydrochloride as a light yellow solid.

Workup

  1. distillationThe solvent was distilled off under reduced pressure, diethyl ether
  2. additionwas added to the resultant residue
  3. filtrationthe solid was filtered off

Sources & evidence

ORD record
ord-60972ebc2c284eab94a07dd6ab71dd11
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

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