Dimethylformamide → HCID 58458900, compound

HRID 390345Notes

Reaction equation

HRID 390345 reaction equation
[CH2:1]([O:8][C:9]1[C:18](=[O:19])[N:17]2[C:12]([C:13]([CH3:21])([CH3:20])[O:14][CH2:15][CH2:16]2)=[N:11][C:10]=1[C:22]([OH:24])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C=O)C.C(Cl)(=O)C(Cl)=O.[NH2:36][NH2:37]>C(Cl)Cl.CCOCC>[CH2:1]([O:8][C:9]1[C:18](=[O:19])[N:17]2[C:12]([C:13]([CH3:20])([CH3:21])[O:14][CH2:15][CH2:16]2)=[N:11][C:10]=1[C:22]([NH:36][NH2:37])=[O:24])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 9321HydrazineHCID 65578Oxalyl chlorideHCID 210698583-(Benzyloxy)-9,9-dimethyl-4-oxo-4,6,7,9-tetrahydropyrimido[2,1-c][1,4]oxazine-2-carboxylic acid

Product 1

HCID 58458900HCID 58458900, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred suspension of 3-(benzyloxy)-9,9-dimethyl-4-oxo-4,6,7,9-tetrahydropyrimido[2,1-c][1,4]oxazine-2-carboxylic acid (prepared according to the procedure in Naidu, B. N. et al WO2005118593) (0.66 g, 2 mmol) in CH2Cl2 (10 mL) containing catalytic DMF was added oxalyl chloride in CH2Cl2 (2 M, 2 mL, 4 mmol) at room temperature. After 3 h, the resulting clear reaction solution was concentrated to remove excess oxalyl chloride. The resulting residue was re-dissolved in CH2Cl2 (20 mL) and treated with anhydrous hydrazine (0.34 mL, 10 mmol). After 2 h at room temperature, the reaction mixture was concentrated and the residue was taken up in EtOAc (100 mL) and washed with sat. NaHCO3 (10 mL), water (10 mL), brine (10 mL) then dried (Na2SO4), filtered and concentrated to give a white solid. This was digested with Et2O (20 mL) and filtered. Concentration of filtrate provided the title compound (0.17 g, 27% yield). 1HNMR (500 MHz, CDCl3) δ: 8.35 (1H, s), 7.55 (2H, d, J=7.3 Hz), 7.38-7.31 (3H, m), 5.30 (2H, s), 4.03-3.97 (6H, m), 1.60 (6H, s). HRMS (M+H) calcd for C17H21N4O5: 345.1563. found: 345.1577.

Workup

  1. customprepared
  2. concentrationthe resulting clear reaction solution was concentrated
  3. customto remove excess oxalyl chloride
  4. dissolutionThe resulting residue was re-dissolved in CH2Cl2 (20 mL)
  5. waitAfter 2 h at room temperature
  6. concentrationthe reaction mixture was concentrated
  7. washwashed with sat. NaHCO3 (10 mL), water (10 mL), brine (10 mL)
  8. dry with materialthen dried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto give a white solid
  12. filtrationfiltered

Sources & evidence

ORD record
ord-d4ab0a45e9d642b6b4f34ba2e67fc176
Source dataset
uspto-grants-2013_02
Patent number
US08383639B2

Reaction notes

Loading…