Hydrogen chloride-ethyl acetate → 1-(2-(4-((7-chloro-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)methylamino)piperidin-1-yl)ethyl)-7-fluoroquinoxalin-2(1H)-one hydrochloride

HRID 39994Notes

Reaction equation

HRID 39994 reaction equation
[Cl:1][C:2]1[C:11]([CH2:12][NH:13][CH:14]2[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][N:22]3[C:31]4[C:26](=[CH:27][CH:28]=[C:29]([F:32])[CH:30]=4)[N:25]=[CH:24][C:23]3=[O:33])[CH2:16][CH2:15]2)=[N:10][C:9]2[NH:8][C:7](=[O:34])[CH2:6][S:5][C:4]=2[CH:3]=1.Cl.C(OCC)(=O)C>C(Cl)(Cl)Cl>[ClH:1].[Cl:1][C:2]1[C:11]([CH2:12][NH:13][CH:14]2[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][N:22]3[C:31]4[C:26](=[CH:27][CH:28]=[C:29]([F:32])[CH:30]=4)[N:25]=[CH:24][C:23]3=[O:33])[CH2:16][CH2:15]2)=[N:10][C:9]2[NH:8][C:7](=[O:34])[CH2:6][S:5][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 593979491-(2-(4-((7-chloro-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)methylamino)piperidin-1-yl)ethyl)-7-fluoroquinoxalin-2(1H)-one

Product 1

HCID 675392011-(2-(4-((7-chloro-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)methylamino)piperidin-1-yl)ethyl)-7-fluoroquinoxalin-2(1H)-one hydrochlorideYield 128.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 5 mL of a chloroform solution containing 452 mg of 1-(2-(4-((7-chloro-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)methylamino)piperidin-1-yl)ethyl)-7-fluoroquinoxalin-2(1H)-one, 1 mL of 4 mol/L hydrogen chloride/ethyl acetate was added, and stirred at room temperature for 10 min. The solvent was removed under reduced pressure, ethyl acetate was added, and the resulting solid was filtered to give 311 mg of 1-(2-(4-((7-chloro-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)methylamino)piperidin-1-yl)ethyl)-7-fluoroquinoxalin-2(1H)-one hydrochloride as a pale brown solid.

Workup

  1. additionwas added
  2. customThe solvent was removed under reduced pressure, ethyl acetate
  3. additionwas added
  4. filtrationthe resulting solid was filtered

Sources & evidence

ORD record
ord-afedec3e559544c98093c04bfb9c9157
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Reaction notes

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