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

HRID 1846998Notes

Reaction equation

HRID 1846998 reaction equation
[NH2:1][CH: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][CH: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 824984066-(4-Amino-2-oxopyrrolidin-1-yl)-2H-1,4-benzoxazin-3(4H)-oneHCID 867249283-(7-Methoxy-2-oxoquinoxalin-1(2H)-yl)propanal

Product 1

HCID 601412936-(4-{[3-(7-Methoxy-2-oxoquinoxalin-1(2H)-yl)propyl]amino}-2-oxopyrrolidin-1-yl)-2H-1,4-benzoxazin-3(4H)-oneYield 97%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

6-(4-Amino-2-oxopyrrolidin-1-yl)-2H-1,4-benzoxazin-3(4H)-one (Reference Example 6; 106 mg, 0.431 mmol) and 3-(7-methoxy-2-oxoquinoxalin-1(2H)-yl)propanal (100 mg, 0.431 mmol) were dissolved in N,N-dimethylformamide (2 ml), and the mixture to which sodium sulfate (400 mg) was added was stirred overnight at room temperature. The reaction solution was diluted with dichloromethane (12 ml), sodium triacetoxyborohydride (110 mg, 0.517 mmol) was added thereto and the mixture was stirred at room temperature for 3 hours. After completion of the reaction, a saturated sodium hydrogen carbonate aqueous solution was added thereto, the organic layer was separated, washed sequentially with saturated sodium chloride solution, 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 193 mg (97%) of the title compound in the form of a light brown solid.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred at room temperature for 3 hours
  3. customAfter completion of the reaction
  4. customthe organic layer was separated
  5. washwashed sequentially with saturated sodium chloride solution, 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-1db0bb88578b4f43b660f503370cf946
Source dataset
uspto-grants-2015_02
Patent number
US08952010B2

Reaction notes

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