Hydrogen chloride-ethyl acetate → 6-{[(1-{2-[7-(methyloxy)-2-oxo-1,5-naphthyridin-1(2H)-yl]ethyl}-4-piperidinyl)amino]methyl}-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one Hydrochloride

HRID 385651Notes

Reaction equation

HRID 385651 reaction equation
[O:1]=[C:2]1[CH2:7][O:6][C:5]2[CH:8]=[CH:9][C:10]([CH2:12][NH:13][CH:14]3[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][N:22]4[C:31]5[C:26](=[N:27][CH:28]=[C:29]([O:32][CH3:33])[CH:30]=5)[CH:25]=[CH:24][C:23]4=[O:34])[CH2:16][CH2:15]3)=[N:11][C:4]=2[NH:3]1.[ClH:35].C(OCC)(=O)C>C(OCC)(=O)C.CO>[ClH:35].[O:1]=[C:2]1[CH2:7][O:6][C:5]2[CH:8]=[CH:9][C:10]([CH2:12][NH:13][CH:14]3[CH2:15][CH2:16][N:17]([CH2:20][CH2:21][N:22]4[C:31]5[C:26](=[N:27][CH:28]=[C:29]([O:32][CH3:33])[CH:30]=5)[CH:25]=[CH:24][C:23]4=[O:34])[CH2:18][CH2:19]3)=[N:11][C:4]=2[NH:3]1

Participants

5

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 250320771-(2-(4-((3-oxo-3,4-dihydro-2H-pyrido(3,2-b)(1,4)oxazin-6-yl)methylamino)piperidin-1-yl)ethyl)-7-methoxy-1,5-naphthyridin-2(1H)-one

Product 1

HCID 689241086-{[(1-{2-[7-(methyloxy)-2-oxo-1,5-naphthyridin-1(2H)-yl]ethyl}-4-piperidinyl)amino]methyl}-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one Hydrochloride

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 260 mg of 1-(2-(4-((3-oxo-3,4-dihydro-2H-pyrido(3,2-b)(1,4)oxazin-6-yl)methylamino)piperidin-1-yl)ethyl)-7-methoxy-1,5-naphthyridin-2(1H)-one in 4 mL of ethyl acetate and 2 mL of methanol, 3 mL of 4 mol/L hydrogen chloride/ethyl acetate was added, and the mixture was stirred at room temperature for 12 minutes. The solvent was distilled off under reduced pressure, thereto was added diethyl ether, and the solid was filtered off to obtain 304 mg of 1-(2-(4-((3-oxo-3,4-dihydro-2H-pyrido(3,2-b)(1,4)oxazin-6-yl)methylamino)piperidin-1-yl)ethyl)-7-methoxy-1,5-naphthyridin-2(1H)-one hydrochloride as a white solid.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. additionwas added diethyl ether
  3. filtrationthe solid was filtered off

Sources & evidence

ORD record
ord-fb23b2b8e707471593a5713cd0d30501
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

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