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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-methoxyquinoxalin-2(1H)-one hydrochloride

HRID 39973
Notes
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Reaction equation

HRID 39973 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]([O:32][CH3:33])[CH:30]=4)[N:25]=[CH:24][C:23]3=[O:34])[CH2:16][CH2:15]2)=[N:10][C:9]2[NH:8][C:7](=[O:35])[CH2:6][S:5][C:4]=2[CH:3]=1.Cl.C(OCC)(=O)C>C(OCC)(=O)C>[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]([O:32][CH3:33])[CH:30]=4)[N:25]=[CH:24][C:23]3=[O:34])[CH2:16][CH2:15]2)=[N:10][C:9]2[NH:8][C:7](=[O:35])[CH2:6][S:5][C:4]=2[CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 593983901-(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-methoxyquinoxalin-2(1H)-one

Product 1

HCID 692897211-(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-methoxyquinoxalin-2(1H)-one hydrochlorideYield 186.8%

Reagents, catalysts & solvents 1

HCID 8857
Ethyl Acetate
Solvent

Procedure

To 12 mL of a chloroform solution containing 609 mg of 1-(2-(4-aminopiperidin-1-yl)ethyl)-7-methoxyquinoxalin-2(1H)-one and 414 mg of 7-chloro-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carbaldehyde, 121 mg of acetic acid was added, and stirred at room temperature for 3 hours. To the reaction mixture, 618 mg of sodium triacetoxyborohydride was added, and stirred for 10.5 hours. Aqueous saturated sodium hydrogen carbonate solution was added, and the organic layer was separated. The organic layer was washed with aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [Silica Gel; Kanto Chemical Co., Inc., Silica Gel 60N, eluent; chloroform: methanol=10:1], to give 0.73 g 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-methoxyquinoxalin-2(1H)-one as a pale yellow foam. To 3 mL of an ethyl acetate solution containing 0.30 g 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-methoxyquinoxalin-2(1H)-one, 2 mL of 4 mol/L hydrogen chloride/ethyl acetate was added, and stirred at room temperature. The resulting solid was filtered to give 300 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-methoxyquinoxalin-2(1H)-one hydrochloride as a pale yellow solid.

Workup

  1. additionwas added
  2. filtrationThe resulting solid was filtered

Sources & evidence

ORD record
ord-766f824232434d508b3ff8157f698c9d
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08524738B2

Reaction notes

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