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Sodium Bicarbonate → 6-(((1-(2-(6-methoxy-3-oxopyrido(2,3-b)pyrazin-4(3H)-yl)ethyl)piperidin-4-yl)amino)methyl)-2H-pyrido(3,2-b)(1,4)thiazin-3(4H)-one

HRID 1510754
Notes
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Reaction equation

HRID 1510754 reaction equation
Cl.[NH2:2][CH:3]1[CH2:8][CH2:7][N:6]([CH2:9][CH2:10][N:11]2[C:16](=[O:17])[CH:15]=[N:14][C:13]3[CH:18]=[CH:19][C:20]([O:22][CH3:23])=[N:21][C:12]2=3)[CH2:5][CH2:4]1.C[O-].[Na+].CO.[O:29]=[C:30]1[CH2:35][S:34][C:33]2[CH:36]=[CH:37][C:38]([CH:40]=O)=[N:39][C:32]=2[NH:31]1.C([BH3-])#N.[Na+].C(=O)([O-])O.[Na+]>CO.C(Cl)(Cl)Cl.C(O)(=O)C>[CH3:23][O:22][C:20]1[CH:19]=[CH:18][C:13]2[N:14]=[CH:15][C:16](=[O:17])[N:11]([CH2:10][CH2:9][N:6]3[CH2:5][CH2:4][CH:3]([NH:2][CH2:40][C:38]4[CH:37]=[CH:36][C:33]5[S:34][CH2:35][C:30](=[O:29])[NH:31][C:32]=5[N:39]=4)[CH2:8][CH2:7]3)[C:12]=2[N:21]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 5

HCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 115935913-Oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carbaldehydeHCID 23694274Sodium methanolate methanolHCID 689298784-(2-(4-aminopiperidin-1-yl)ethyl)-6-methoxypyrido(2,3-b)pyrazin-3(4H)-one hydrochloride

Product 1

HCID 57815516
6-(((1-(2-(6-methoxy-3-oxopyrido(2,3-b)pyrazin-4(3H)-yl)ethyl)piperidin-4-yl)amino)methyl)-2H-pyrido(3,2-b)(1,4)thiazin-3(4H)-one
Yield 47.7%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

To a suspension of 0.21 g of 4-(2-(4-aminopiperidin-1-yl)ethyl)-6-methoxypyrido(2,3-b)pyrazin-3(4H)-one hydrochloride in 5 mL of methanol, 0.22 g of a 28% sodium methoxide/methanol solution, 0.11 g of 3-oxo-3,4-dihydro-2H-pyrido(3,2-b)(1,4)thiazine-6-carbaldehyde, 32 μL of acetic acid and 70 mg of sodium cyanoborohydride were added, and the mixture was stirred at room temperature for 3 hours. Chloroform and a saturated aqueous sodium hydrogen carbonate solution were added to the reaction mixture, the organic layer was separated, and the aqueous layer was extracted with chloroform. The organic layer and the extract were combined, the resultant solution was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The resultant residue was purified by basic silica gel column chromatography using an eluent of chloroform:methanol=10:1. Diethyl ether and hexane were added to the resultant residue, and the solid was filtered off to obtain 0.13 g of 6-(((1-(2-(6-methoxy-3-oxopyrido(2,3-b)pyrazin-4(3H)-yl)ethyl)piperidin-4-yl)amino)methyl)-2H-pyrido(3,2-b)(1,4)thiazin-3(4H)-one as a light brown solid.

Workup

  1. additionwere added
  2. customthe organic layer was separated
  3. extractionthe aqueous layer was extracted with chloroform
  4. washthe resultant solution was washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe resultant residue was purified by basic silica gel column chromatography
  8. additionDiethyl ether and hexane were added to the resultant residue
  9. filtrationthe solid was filtered off

Sources & evidence

ORD record
ord-d6b29f9ab0034842a7d15214eff9386a
Source dataset
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08211908B2

Reaction notes

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