Sodium Methoxide → 8-(2,5-Dimethyl-phenyl)-3-methoxy-tetrahydro-pyrazolo[1,2-a][1,2,5]triazepine-7,9-dione

HRID 924605Notes

Reaction equation

HRID 924605 reaction equation
C(O[C:4]([N:6]1[CH2:12][CH2:11][N:10]([O:13][CH3:14])[CH2:9][CH2:8][N:7]1[C:15](=[O:25])[CH2:16][C:17]1[CH:22]=[C:21]([CH3:23])[CH:20]=[CH:19][C:18]=1[CH3:24])=[O:5])C.C[O-].[Na+]>CN(C)C=O>[CH3:24][C:18]1[CH:19]=[CH:20][C:21]([CH3:23])=[CH:22][C:17]=1[CH:16]1[C:4](=[O:5])[N:6]2[CH2:12][CH2:11][N:10]([O:13][CH3:14])[CH2:9][CH2:8][N:7]2[C:15]1=[O:25]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 867199182-[2-(2,5-Dimethyl-phenyl)-acetyl]-5-methoxy-[1,2,5]triazepane-1-carboxylic acid ethyl ester

Product 1

HCID 867199218-(2,5-Dimethyl-phenyl)-3-methoxy-tetrahydro-pyrazolo[1,2-a][1,2,5]triazepine-7,9-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-[2-(2,5-dimethyl-phenyl)-acetyl]-5-methoxy-[1,2,5]triazepane-1-carboxylic acid ethyl ester (800 mg, 2.29 mmol) in absolute dimethylformamide (10 ml) at 10° C. was added sodium methoxide (371 mg, 6.87 mmol) in one portion and stirring continued at 10° C. for 30 minutes, then at room temperature for two hours. The solvent was evaporated in vacuo, the residue diluted in cold water (10 ml), acidified to pH 5 with 2N HCl and thoroughly extracted with ethyl acetate. The combined organic layers were washed with brine (3×15 ml), dried over sodium sulfate and concentrated. The residue was triturated with diethyl ether, filtered, washed with cold ether and dried in vacuo. Yield: 450 mg of 8-(2,5-dimethyl-phenyl)-3-methoxy-tetrahydro-pyrazolo[1,2-a][1,2,5]triazepine-7,9-dione (title compound P2.4) as an off-white solid, mp 167-169° C.

Workup

  1. waitat room temperature for two hours
  2. customThe solvent was evaporated in vacuo
  3. additionthe residue diluted in cold water (10 ml)
  4. extractionthoroughly extracted with ethyl acetate
  5. washThe combined organic layers were washed with brine (3×15 ml)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customThe residue was triturated with diethyl ether
  9. filtrationfiltered
  10. washwashed with cold ether
  11. customdried in vacuo

Sources & evidence

ORD record
ord-1671db0a98e946c5bfa9ee3fda171aa7
Source dataset
uspto-grants-2016_03
Patent number
US09282743B2

Reaction notes

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