Sodium Bicarbonate → HCID 59398301, compound

HRID 40005Notes

Reaction equation

HRID 40005 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([N:7]=[CH:8][C:9](=[O:26])[N:10]2[CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][C:18](=O)[CH2:17][CH:16]2[C:22]([O:24][CH3:25])=[O:23])=[CH:5][CH:4]=1.[O:27]1[C:36]2[CH:35]=[C:34]([CH2:37][NH2:38])[N:33]=[CH:32][C:31]=2[O:30][CH2:29][CH2:28]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.C(O)(=O)C.ClCCl>[O:27]1[C:36]2[CH:35]=[C:34]([CH2:37][NH:38][CH:18]3[CH2:19][CH2:20][N:15]([CH2:14][CH2:13][N:10]4[C:11]5[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:12]=5)[N:7]=[CH:8][C:9]4=[O:26])[CH:16]([C:22]([O:24][CH3:25])=[O:23])[CH2:17]3)[N:33]=[CH:32][C:31]=2[O:30][CH2:29][CH2:28]1

Participants

8

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 59397860HCID 59397860, compoundHCID 593981871-(2,3-Dihydro[1,4]dioxino[2,3-c]pyridin-7-yl)methanamine

Product 1

HCID 59398301HCID 59398301, compoundYield 45.1%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolvent2×HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent2×

Procedure

To 10 mL of a dichloromethane solution containing 0.10 g of methyl 1-(2-(7-methoxy-2-oxoquinoxalin-1(2H)-yl)ethyl)-4-oxopiperidine-2-carboxylate, 2 mL of a dichloromethane solution containing 55 mg of 1-(2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-yl)methaneamine and 32 μL of acetic acid were added at room temperature, and stirred at the same temperature for 1 hour, thereafter, 8 μL of acetic acid was further added, and stirred for 2.5 hours. To the reaction mixture, 59 mg of sodium triacetoxyborohydride was added, and stirred for 1 hour. To the reaction mixture, aqueous saturated sodium hydrogen carbonate solution and chloroform were added. The organic layer was separated, 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 basic silica gel column chromatography [eluent; chloroform:methanol=50:1], to give 64 mg of methyl 4-((2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-ylmethyl)amino)-1-(2-(7-methoxy-2-oxoquinoxalin-1(2H)-yl)ethyl)piperidine-2-carboxylate as a white foam.

Workup

  1. additionwere added at room temperature
  2. stirringstirred for 2.5 hours
  3. stirringstirred for 1 hour
  4. customThe organic layer was separated
  5. washwashed with aqueous saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was removed under reduced pressure
  8. customThe residue thus obtained
  9. customwas purified by basic silica gel column chromatography [eluent; chloroform:methanol=50:1]

Sources & evidence

ORD record
ord-23e7553599df4bf0806ea65114cc039a
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Reaction notes

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