Sodium Sulfate → HCID 86724970, compound

HRID 1847045Notes

Reaction equation

HRID 1847045 reaction equation
S([O-])([O-])(=O)=O.[Na+].[Na+].[CH3:8][O:9][C:10]1[CH:19]=[C:18]2[C:13]([N:14]=[CH:15][C:16](=[O:23])[N:17]2[CH2:20][CH:21]=O)=[CH:12][CH:11]=1.[NH2:24][CH2:25][C@@H:26]1[CH2:30][N:29]([C:31]2[CH:32]=[CH:33][C:34]3[O:39][CH2:38][C:37](=[O:40])[NH:36][C:35]=3[CH:41]=2)[C:28](=[O:42])[CH2:27]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>ClCCl.O.CN(C)C=O>[CH3:8][O:9][C:10]1[CH:19]=[C:18]2[C:13]([N:14]=[CH:15][C:16](=[O:23])[N:17]2[CH2:20][CH2:21][NH:24][CH2:25][C@@H:26]2[CH2:30][N:29]([C:31]3[CH:32]=[CH:33][C:34]4[O:39][CH2:38][C:37](=[O:40])[NH:36][C:35]=4[CH:41]=3)[C:28](=[O:42])[CH2:27]2)=[CH:12][CH:11]=1

Participants

9

Reactant 5

HCID 24436Sodium SulfateHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 59398142(7-methoxy-2-oxoquinoxalin-1(2H)-yl)acetaldehydeHCID 86724969HCID 86724969, compound

Product 1

HCID 86724970HCID 86724970, compoundYield 90.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent3×

Procedure

Under a nitrogen gas atmosphere, anhydrous sodium sulfate (1.4 g) was added at room temperature to a solution of (7-methoxy-2-oxoquinoxalin-1(2H)-yl)acetaldehyde (synthesized with reference to WO2009/1126; 167 mg, 0.765 mmol) and 6-[(4R)-4-(aminomethyl)-2-oxopyrrolidin-1-yl]-2H-1,4-benzoxazin-3(4H)-one (200 mg, 0.765 mmol) in dichloromethane (3 ml)/N,N-dimethylformamide (1 ml) and the mixture was stirred at the same temperature for 2 hours. Dichloromethane (3 ml) was added to the reaction solution, sodium triacetoxyborohydride (243 mg, 1.15 mmol) was subsequently added thereto and the mixture was stirred at the same temperature for 15 hours. Water (10 ml) was added to the reaction solution to dissolve the insoluble material and then a mixture of dichloromethane and a saturated sodium hydrogen carbonate aqueous solution was poured thereinto and the resultant was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate, the drying agent was removed by filtration and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (dichloromethane/methanol) to yield 321 mg (90%) of the title compound in the form of a light yellow amorphous solid.

Workup

  1. additionwas subsequently added
  2. stirringthe mixture was stirred at the same temperature for 15 hours
  3. dissolutionto dissolve the insoluble material
  4. extractionthe resultant was extracted with dichloromethane
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customthe drying agent was removed by filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (dichloromethane/methanol)

Sources & evidence

ORD record
ord-e79fdd487ab348f79b4c271842cfcc1c
Source dataset
uspto-grants-2015_02
Patent number
US08952010B2

Reaction notes

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