Sodium Bicarbonate → HCID 59397957, compound

HRID 2193380Notes

Reaction equation

HRID 2193380 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][N:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([O:20][CH3:21])[CH:18]=3)[N:13]=[CH:12][C:11]2=[O:22])[CH2:4][CH2:3]1.[C:23]([O:27][C:28](=[O:39])[NH:29][C:30]1[CH:35]=[C:34]([CH:36]=O)[CH:33]=[CH:32][C:31]=1[CH3:38])([CH3:26])([CH3:25])[CH3:24].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.C(Cl)Cl>[C:23]([O:27][C:28](=[O:39])[NH:29][C:30]1[CH:35]=[C:34]([CH2:36][NH:1][CH:2]2[CH2:3][CH2:4][N:5]([CH2:8][CH2:9][N:10]3[C:19]4[C:14](=[CH:15][CH:16]=[C:17]([O:20][CH3:21])[CH:18]=4)[N:13]=[CH:12][C:11]3=[O:22])[CH2:6][CH2:7]2)[CH:33]=[CH:32][C:31]=1[CH3:38])([CH3:26])([CH3:25])[CH3:24]

Participants

8

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride3×HCID 593978381-[2-(4-Aminopiperidin-1-yl)ethyl]-7-methoxyquinoxalin-2(1H)-oneHCID 59398258HCID 59398258, compound

Product 1

HCID 59397957HCID 59397957, compoundYield 81.2%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolvent3×HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To 10 mL of a methylene chloride solution containing 0.20 g of 1-(2-(4-aminopiperidin-1-yl)ethyl)-7-methoxyquinoxalin-2(1H)-one, 0.19 g of tert-butyl(5-formyl-2-methylphenyl)carbamate and 45 μL of acetic acid were added, and stirred for 30 min. To the reaction mixture, 0.21 g of sodium triacetoxyborohydride was added, and stirred for 10 hours. After allowed to stand overnight, 45 μl of acetic acid was added and stirred for 40 min, then 0.17 g of sodium triacetoxyborohydride was added, and stirred at room temperature for 2 hours and 40 min. 90 μL of acetic acid was further added and stirred for 40 min, then 0.34 g of sodium triacetoxyborohydride was added, and stirred at room temperature for 2 hours. 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, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [eluent; chloroform:methanol=5:1], to give 0.28 g of tert-butyl(5-(((1-(2-(7-methoxy-2-oxoquinoxalin-1(2H)-yl)ethyl)piperidin-4-yl)amino)methyl)-2-methylphenyl)carbamate as a pale yellow oil.

Workup

  1. additionwere added
  2. stirringstirred for 10 hours
  3. waitto stand overnight
  4. stirringstirred for 40 min
  5. stirringstirred at room temperature for 2 hours and 40 min
  6. stirringstirred for 40 min
  7. stirringstirred at room temperature for 2 hours
  8. customthe organic layer was separated
  9. extractionthe aqueous layer was extracted with chloroform
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customthe solvent was removed under reduced pressure
  12. customThe residue thus obtained
  13. customwas purified by silica gel column chromatography [eluent; chloroform:methanol=5:1]

Sources & evidence

ORD record
ord-a4458763c4e74d94a5ec125b69b366e5
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Reaction notes

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