Sodium Bicarbonate → HCID 60162050, compound

HRID 1847096Notes

Reaction equation

HRID 1847096 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([CH3:18])=[CH:8][C:9](=[O:17])[N:10]2[CH2:13][CH2:14][CH:15]=O)=[CH:5][CH:4]=1.[NH2:19][C@H:20]1[CH2:24][N:23]([C:25]2[CH:26]=[CH:27][C:28]3[O:29][CH2:30][C:31](=[O:35])[NH:32][C:33]=3[N:34]=2)[C:22](=[O:36])[CH2:21]1.C(OC(=O)N[C@@H]1CC(=O)NC1)(C)(C)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([CH3:18])=[CH:8][C:9](=[O:17])[N:10]2[CH2:13][CH2:14][CH2:15][NH:19][C@H:20]2[CH2:24][N:23]([C:25]3[CH:26]=[CH:27][C:28]4[O:29][CH2:30][C:31](=[O:35])[NH:32][C:33]=4[N:34]=3)[C:22](=[O:36])[CH2:21]2)=[CH:5][CH:4]=1

Participants

7

Reactant 5

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 71301758tert-Butyl [(3R)-5-oxopyrrolidin-3-yl]carbamateHCID 867249916-[(4R)-4-amino-2-oxopyrrolidin-1-yl]-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-oneHCID 867250173-(7-Methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)propanal

Product 1

HCID 60162050HCID 60162050, compoundYield 3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)propanal (150 mg, 1.13 mmol) in N,N-dimethylformamide (5 ml) was added 6-[(4R)-4-amino-2-oxopyrrolidin-1-yl]-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one (synthesized using [(3R)-5-oxopyrrolidin-3-yl]carbamic acid tert-butyl ester synthesized with reference to WO2004/22536 in the same manner as in Reference Examples 20, 21 and 22; 303 mg, 1.22 mmol) and the mixture was stirred at room temperature for 1 hour. After cooling the reaction solution on ice, sodium triacetoxyborohydride (388 mg, 1.83 mmol) was added thereto and the mixture was stirred at room temperature for 2 hours. A sodium hydrogen carbonate aqueous solution was added, the reaction solution was extracted with ethyl acetate and the extract was washed with water and saturated sodium chloride solution. The obtained organic layer was dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The obtained crude product was purified by thin layer chromatography (dichloromethane/methanol) so as to yield 15 mg (3%) of the title compound.

Workup

  1. customsynthesized
  2. customsynthesized with reference to WO2004/22536 in the same manner as in Reference Examples 20, 21 and 22
  3. additionwas added
  4. stirringthe mixture was stirred at room temperature for 2 hours
  5. extractionthe reaction solution was extracted with ethyl acetate
  6. washthe extract was washed with water and saturated sodium chloride solution
  7. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
  8. customthe solvent was removed under reduced pressure
  9. customThe obtained crude product
  10. customwas purified by thin layer chromatography (dichloromethane/methanol) so as

Sources & evidence

ORD record
ord-02ad4c5b205d4483943fd9b5c816a2f3
Source dataset
uspto-grants-2015_02
Patent number
US08952010B2

Reaction notes

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