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

HRID 1847030Notes

Reaction equation

HRID 1847030 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+]>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

7

Reactant 5

HCID 24436Sodium SulfateHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 867249283-(7-Methoxy-2-oxoquinoxalin-1(2H)-yl)propanalHCID 867249576-[(4R)-4-Amino-2-oxopyrrolidin-1-yl]-2H-1,4-benzoxazin-3(4H)-one

Product 1

HCID 601617766-[(4R)-4-{[3-(7-Methoxy-2-oxoquinoxalin-1(2H)-yl)propyl]amino}-2-oxopyrrolidin-1-yl]-2H-1,4-benzoxazin-3(4H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-[(4R)-4-Amino-2-oxopyrrolidin-1-yl]-2H-1,4-benzoxazin-3(4H)-one (23.9 mg, 0.0967 mmol) and 3-(7-methoxy-2-oxoquinoxalin-1(2H)-yl)propanal (Reference Example 8; 22.4 mg, 0.0967 mmol) were dissolved in N,N-dimethylfomamide (0.5 ml). Sodium sulfate (100 mg) was added to the obtained solution, and the mixture was then stirred at room temperature overnight. Thereafter, sodium triacetoxy borohydride (30.7 mg, 0.145 mmol) was added to the reaction solution, and the obtained mixture was then 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 (4×) and saturated sodium chloride solution, and was then dried over anhydrous magnesium sulfate. Thereafter, the solvent was removed under reduced pressure. The obtained residue was purified by preparative thin layer chromatography (chloroform/methanol) to yield 18.4 mg (41%) of the above captioned compound in the form of a light brown solid.

Workup

  1. stirringthe obtained mixture was then stirred at room temperature for 2 days
  2. customthe organic layer was separated
  3. washThe organic layer was washed with water (4×) and saturated sodium chloride solution
  4. dry with materialwas then dried over anhydrous magnesium sulfate
  5. customThereafter, the solvent was removed under reduced pressure
  6. customThe obtained residue was purified by preparative thin layer chromatography (chloroform/methanol)
  7. customto yield 18.4 mg (41%) of the

Sources & evidence

ORD record
ord-d9677f2d28cc478ead824941648369ec
Source dataset
uspto-grants-2015_02
Patent number
US08952010B2

Reaction notes

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