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 2193374Notes

Reaction equation

HRID 2193374 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-450b7849a8f34cef94ee0217d627c77c
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Reaction notes

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