Sodium Sulfate → 6-(4-{[4-(7-Methoxy-2-oxoquinoxalin-1(2H)-yl)butyl]amino}-2-oxopyrrolidin-1-yl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one

HRID 1847032Notes

Reaction equation

HRID 1847032 reaction equation
[NH2:1][CH:2]1[CH2:6][N:5]([C:7]2[CH:8]=[CH:9][C:10]3[O:11][CH2:12][C:13](=[O:17])[NH:14][C:15]=3[N:16]=2)[C:4](=[O:18])[CH2:3]1.[CH3:19][O:20][C:21]1[CH:30]=[C:29]2[C:24]([N:25]=[CH:26][C:27](=[O:36])[N:28]2[CH2:31][CH2:32][CH2:33][CH:34]=O)=[CH:23][CH:22]=1.S([O-])([O-])(=O)=O.[Na+].[Na+].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>CN(C)C=O.ClCCl>[CH3:19][O:20][C:21]1[CH:30]=[C:29]2[C:24]([N:25]=[CH:26][C:27](=[O:36])[N:28]2[CH2:31][CH2:32][CH2:33][CH2:34][NH:1][CH:2]2[CH2:6][N:5]([C:7]3[CH:8]=[CH:9][C:10]4[O:11][CH2:12][C:13](=[O:17])[NH:14][C:15]=4[N:16]=3)[C:4](=[O:18])[CH2:3]2)=[CH:23][CH:22]=1

Participants

8

Reactant 5

HCID 24436Sodium SulfateHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 867249234-(7-Methoxy-2-oxoquinoxalin-1(2H)-yl)butanalHCID 867249416-(4-Amino-2-oxopyrrolidin-1-yl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one

Product 1

HCID 601620476-(4-{[4-(7-Methoxy-2-oxoquinoxalin-1(2H)-yl)butyl]amino}-2-oxopyrrolidin-1-yl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-oneYield 77.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

6-(4-Amino-2-oxopyrrolidin-1-yl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one (Reference Examples 19; 67 mg, 0.250 mmol) and 4-(7-methoxy-2-oxoquinoxalin-1(2H)-yl)butanal (Reference Examples 3; 58 mg, 0.250 mmol) were dissolved in N,N-dimethylformamide (4 ml). Sodium sulfate (800 mg) was added to this solution and the mixture was stirred at room temperature for 8 hours. Sodium triacetoxyborohydride (80 mg, 0.375 mmol) was added to the reaction solution and the mixture was stirred overnight at room temperature. After completion of the reaction, the reaction solution was diluted with dichloromethane, a saturated sodium hydrogen carbonate aqueous solution was added thereto and the mixture was stirred for 10 minutes. The organic layer was separated, washed sequentially with water (3×) and saturated sodium chloride solution, dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform/methanol) to yield 93 mg (76%) of the title compound in the form of a yellow solid.

Workup

  1. stirringthe mixture was stirred overnight at room temperature
  2. customAfter completion of the reaction
  3. stirringthe mixture was stirred for 10 minutes
  4. customThe organic layer was separated
  5. washwashed sequentially with water (3×) and saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was removed under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-5dcc6f9e27724428b257a905c2216ed5
Source dataset
uspto-grants-2015_02
Patent number
US08952010B2

Reaction notes

Loading…