Sodium Sulfate → 6-[(4S)-4-{[3-(7-methoxy-2-oxoquinoxalin-1(2H)-yl)propyl]amino}-2-oxopyrrolidin-1-yl]-2H-1,4-benzoxazin-3(4H)-one

HRID 1847035Notes

Reaction equation

HRID 1847035 reaction equation
[NH2:1][C@@H:2]1[CH2:6][N:5]([C:7]2[CH:8]=[CH:9][C:10]3[O:15][CH2:14][C:13](=[O:16])[NH:12][C:11]=3[CH:17]=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:35])[N:28]2[CH2:31][CH2:32][CH:33]=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:35])[N:28]2[CH2:31][CH2:32][CH2:33][NH:1][C@@H:2]2[CH2:6][N:5]([C:7]3[CH:8]=[CH:9][C:10]4[O:15][CH2:14][C:13](=[O:16])[NH:12][C:11]=4[CH:17]=3)[C:4](=[O:18])[CH2:3]2)=[CH:23][CH:22]=1

Participants

8

Reactant 5

HCID 24436Sodium SulfateHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 867249283-(7-Methoxy-2-oxoquinoxalin-1(2H)-yl)propanalHCID 867249596-[(4S)-4-Amino-2-oxopyrrolidin-1-yl]-2H-1,4-benzoxazin-3(4H)-one

Product 1

HCID 601616406-[(4S)-4-{[3-(7-methoxy-2-oxoquinoxalin-1(2H)-yl)propyl]amino}-2-oxopyrrolidin-1-yl]-2H-1,4-benzoxazin-3(4H)-oneYield 58%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

6-[(4S)-4-Amino-2-oxopyrrolidin-1-yl]-2H-1,4-benzoxazin-3(4H)-one (330 mg, 1.21 mmol) and 3-(7-methoxy-2-oxoquinoxalin-1(2H)-yl)propanal (Reference Example 8; 281 mg, 1.21 mmol) were dissolved in N,N-dimethylformamide (8.8 ml). Sodium sulfate (1.4 g) was added to this solution and the mixture was stirred at room temperature for 5.5 hours. Sodium triacetoxyborohydride (386 mg, 1.82 mmol) was added to the reaction solution and the mixture was stirred at room temperature for 2 days. After completion of the reaction, dichloromethane and a saturated sodium hydrogen carbonate aqueous solution were added to the reaction solution and the organic layer was separated. The organic layer was washed 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 flash column chromatography (chloroform/methanol) to yield 324 mg (58%) of the title compound in the form of light brown foamy crystals.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 days
  2. customthe organic layer was separated
  3. washThe organic layer was washed with water (3×) and saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe obtained residue was purified by flash column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-9285775d764949a1acf09fea163187e8
Source dataset
uspto-grants-2015_02
Patent number
US08952010B2

Reaction notes

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