Sodium Hydroxide → HCID 59829805, compound

HRID 1947200Notes

Reaction equation

HRID 1947200 reaction equation
[OH-:1].[Na+].[CH:3]([C:6]1[C:7]([O:38][CH2:39][O:40][CH3:41])=[CH:8][C:9]([O:34][CH2:35][O:36][CH3:37])=[C:10]([C:12]2[N:16]([C:17]3[CH:22]=[CH:21][C:20]([CH2:23][N:24]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)=[CH:19][CH:18]=3)[C:15](S(C)(=O)=O)=[N:14][N:13]=2)[CH:11]=1)([CH3:5])[CH3:4]>CS(C)=O>[CH:3]([C:6]1[C:7]([O:38][CH2:39][O:40][CH3:41])=[CH:8][C:9]([O:34][CH2:35][O:36][CH3:37])=[C:10]([C:12]2[N:16]([C:17]3[CH:22]=[CH:21][C:20]([CH2:23][N:24]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)=[CH:19][CH:18]=3)[C:15](=[O:1])[NH:14][N:13]=2)[CH:11]=1)([CH3:5])[CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59829790HCID 59829790, compound

Product 1

HCID 59829805HCID 59829805, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

At room temperature aqueous sodium hydroxide (1.0 M aqueous solution, 7 mL) was added to a dimethylsulfoxide solution (7 mL) of the crude product (1.01 g), which was obtained in the previous step, containing 3-(5-isopropyl-2,4-bis-methoxymethoxyphenyl)-4-(4-molpholin-4-ylmethylphenyl)-5-methanesulfonyl-4H-[1,2,4]triazole (F45-05). The reaction mixture was heated at 90° C. for 5.5 hours while stirring, cooled to room temperature, extracted with ethyl acetate, and the extract was washed twice with water and then saturated sodium chloride solution. The extract was dried over anhydrous sodium sulfate, and then sodium sulfate was removed by filtration. The solvent was distilled off under reduced pressure to obtain a pale yellow foam. Reprecipitation purification was carried out (chloroform, diethyl ether), and the solids were washed with diethyl ether and dried under reduced pressure to obtain 5-(5-isopropyl-2,4-bis-methoxymethoxyphenyl)-4-(4-morpholin-4-ylmethylphenyl)-2,4-dihydro-[1,2,4]triazole-3-one (F45-06, pale yellow solid, 469 mg, 53%).

Workup

  1. customwhich was obtained in the previous step
  2. temperaturecooled to room temperature
  3. extractionextracted with ethyl acetate
  4. washthe extract was washed twice with water
  5. dry with materialThe extract was dried over anhydrous sodium sulfate
  6. customsodium sulfate was removed by filtration
  7. distillationThe solvent was distilled off under reduced pressure
  8. customto obtain a pale yellow foam
  9. customReprecipitation purification
  10. washthe solids were washed with diethyl ether
  11. customdried under reduced pressure

Sources & evidence

ORD record
ord-f9110d710b9b4805bced51fad62d4c22
Source dataset
uspto-grants-2013_03
Patent number
US08399464B2

Reaction notes

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