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Acetonitrile → ethyl((2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-ylmethyl)(1-(2-(7-methoxy-2-oxo-1,5-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)amino)acetate

HRID 385653
Notes
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Reaction equation

HRID 385653 reaction equation
[O:1]1[C:10]2[CH:9]=[C:8]([CH2:11][NH:12][CH:13]3[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][N:21]4[C:30]5[C:25](=[N:26][CH:27]=[C:28]([O:31][CH3:32])[CH:29]=5)[CH:24]=[CH:23][C:22]4=[O:33])[CH2:15][CH2:14]3)[N:7]=[CH:6][C:5]=2[O:4][CH2:3][CH2:2]1.[C:34]([O:37]Br)(=[O:36])[CH3:35].C(=O)([O-])[O-].[K+].[K+].[C:45](#N)[CH3:46]>>[O:1]1[C:10]2[CH:9]=[C:8]([CH2:11][N:12]([CH2:35][C:34]([O:37][CH2:45][CH3:46])=[O:36])[CH:13]3[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][N:21]4[C:30]5[C:25](=[N:26][CH:27]=[C:28]([O:31][CH3:32])[CH:29]=5)[CH:24]=[CH:23][C:22]4=[O:33])[CH2:15][CH2:14]3)[N:7]=[CH:6][C:5]=2[O:4][CH2:3][CH2:2]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 10986304Bromo acetateHCID 578152671-[2-[4-(2,3-Dihydro-[1,4]dioxino[2,3-c]pyridin-7-ylmethylamino)-1-piperidyl]ethyl]-7-methoxy-1,5-naphthyridin-2-one

Product 1

HCID 57815482ethyl((2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-ylmethyl)(1-(2-(7-methoxy-2-oxo-1,5-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)amino)acetate

Procedure

A solution of 150 mg of 1-(2-(4-((2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-yl)methylamino)piperidin-1-yl)ethyl)-7-methoxy-1,5-naphthyridin-2(1H)-one and 85 mg of bromo acetate in 15 mL of acetonitrile, 100 mg of potassium carbonate was added, and the mixture was stirred at room temperature for 18 hours, and stirred at 40° C. for 4 hours. The solvent was distilled off under reduced pressure, thereto were added chloroform and water, and the organic layer was separated. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The resultant residue was purified by silica gel column chromatography using silica gel; Silica Gel 60N made by KANTO CHEMICAL CO., INC., and an eluent of chloroform:methanol=20:1 to obtain 90 mg of ethyl ((2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-ylmethyl)(1-(2-(7-methoxy-2-oxo-1,5-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)amino)acetate as an brown oily substance.

Workup

  1. stirringstirred at 40° C. for 4 hours
  2. distillationThe solvent was distilled off under reduced pressure
  3. additionwere added chloroform and water
  4. customthe organic layer was separated
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe resultant residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f0e2943a7f614c2989462eb6b21f29b5
Source dataset
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08367831B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes