Sodium Bicarbonate → HCID 59398257, compound

HRID 40007Notes

Reaction equation

HRID 40007 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.C([O-])(=O)C.[NH4+].C([BH3-])#[N:33].[Na+].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.C(O)C>[NH2:33][CH:18]1[CH2:19][CH2:20][N:15]([CH2:14][CH2:13][N:10]2[C:11]3[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:12]=3)[N:7]=[CH:8][C:9]2=[O:26])[CH:16]([C:22]([O:24][CH3:25])=[O:23])[CH2:17]1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 59397860HCID 59397860, compound

Product 1

HCID 59398257HCID 59398257, compoundYield 91.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent

Procedure

To 5 mL of an ethanol suspension containing 0.15 g of methyl 1-(2-(7-methoxy-2-oxoquinoxalin-1(2H)-yl)ethyl)-4-oxopiperidine-2-carboxylate, 0.16 g of ammonium acetate and 0.20 g of molecular sieves 3A were added at room temperature. After the mixture was stirred for 2 hours and 55 min at room temperature, 21 mg of sodium cyanoborohydride was added, and stirred for 1 hour and 40 min. To the reaction mixture, aqueous saturated sodium hydrogen carbonate solution and chloroform were added, the organic layer was separated, and the aqueous layer was extracted with chloroform. The organic layer and extracts were combined, washed with aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to give 0.11 g of methyl 4-amino-1-(2-(7-methoxy-2-oxoquinoxalin-1(2H)-yl)ethyl)piperidine-2-carboxylate as a brown foam. (2) According to a procedure similar to Example 179, methyl 4-((3-fluoro-4-methylbenzyl)amino-1-(2-(7-methoxy-2-oxoquinoxalin-1(2H)-yl)ethyl)piperidine-2-carboxylate was obtained from methyl 4-amino-1-(2-(7-methoxy-2-oxoquinoxalin-1(2H)-yl)ethyl)piperidine-2-carboxylate.

Workup

  1. additionwere added at room temperature
  2. stirringstirred for 1 hour and 40 min
  3. customthe organic layer was separated
  4. extractionthe aqueous layer was extracted with chloroform
  5. washwashed with aqueous saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-fd96fa3f8735446bbb097d0adb1d62ce
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Reaction notes

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