Hydrochloric Acid → HCID 86719925, compound

HRID 924609Notes

Reaction equation

HRID 924609 reaction equation
C([O:3][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:27])[CH2:16][C:17]1[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[CH:19][C:18]=1[CH2:25][CH3:26])=O)C.C[O-].[Na+].Cl>CN(C)C=O>[CH2:25]([C:18]1[CH:19]=[C:20]([CH3:24])[CH:21]=[C:22]([CH3:23])[C:17]=1[CH:16]1[C:15](=[O:27])[N:7]2[CH2:8][CH2:9][N:10]([O:13][CH3:14])[CH2:11][CH2:12][N:6]2[C:4]1=[O:3])[CH3:26]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 86719926HCID 86719926, compound

Product 1

HCID 86719925HCID 86719925, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-[2-(2-ethyl-4,6-dimethyl-phenyl)-acetyl]-5-methoxy-[1,2,5]triazepane-1-carboxylic acid ethyl ester (550 mg, 1.46 mmol) in absolute dimethylformamide (5 ml) at 80° C. was added sodium methoxide (240 mg, 4.44 mmol) in one portion and stirring continued at 80° C. for 20 minutes. The cooled reaction mixture was poured on ice, the aqueous alkaline phase was acidified to pH 5 by addition of a 6N HCl solution, the resulting suspension was filtered, the obtained solid dissolved in dichloromethane, the organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by chromatography on silica gel (ethyl acetate/methanol 20:1). Yield: 220 mg of 8-(2-ethyl-4,6-dimethyl-phenyl)-3-methoxy-tetrahydro-pyrazolo[1,2-a][1,2,5]triazepine-7,9-dione (compound P2.14) as a pale brown solid, mp 213-215° C.

Workup

  1. customThe cooled reaction mixture
  2. additionwas poured on ice
  3. filtrationthe resulting suspension was filtered
  4. dissolutionthe obtained solid dissolved in dichloromethane
  5. dry with materialthe organic layer was dried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by chromatography on silica gel (ethyl acetate/methanol 20:1)

Sources & evidence

ORD record
ord-81d5892727254e208ff73c4841b8d343
Source dataset
uspto-grants-2016_03
Patent number
US09282743B2

Reaction notes

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