Hydrochloric Acid → HCID 136159956, compound

HRID 1947226Notes

Reaction equation

HRID 1947226 reaction equation
[CH:1]([C:4]1[C:5]([O:36]COC)=[CH:6][C:7]([O:32]COC)=[C:8]([C:10]2[N:11]([C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=3)[C:12]([S:15]([CH2:18][CH2:19][CH2:20][N:21]([CH3:23])[CH3:22])(=[O:17])=[O:16])=[N:13][N:14]=2)[CH:9]=1)([CH3:3])[CH3:2].Cl.C(=O)([O-])O.[Na+]>C(O)C>[CH3:23][N:21]([CH3:22])[CH2:20][CH2:19][CH2:18][S:15]([C:12]1[N:11]([C:24]2[CH:25]=[CH:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=2)[C:10]([C:8]2[CH:9]=[C:4]([CH:1]([CH3:3])[CH3:2])[C:5]([OH:36])=[CH:6][C:7]=2[OH:32])=[N:14][N:13]=1)(=[O:17])=[O:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 59829817HCID 59829817, compound

Product 1

HCID 136159956HCID 136159956, compoundYield 35.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

{3-[5-(5-isopropyl-2,4-bis-methoxymethoxy-phenyl)-4-(4-methoxy-phenyl)-4H-[1,2,4]triazole-3-sulfonyl]-propyl}-dimethylamine (6.8 g, crude F68-02 in the previous step), ethanol (50 mL) and 3 N hydrochloric acid (50 mL) were placed in a 200 mL eggplant shaped flask and the mixture was stirred at 50° C. for 5 hours. After completing the reaction, the reaction mixture was neutralized with saturated sodium hydrogencarbonate, extracted twice with ethyl acetate. The organic layer was washed 4 times with saturated sodium chloride, dried with sodium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride/methanol), followed by basic silica gel column chromatography (methylene chloride/methanol) to obtain the title compound (F68-03: 1.5 g, 35.7% in 2 steps)

Workup

  1. customthe reaction
  2. extractionextracted twice with ethyl acetate
  3. washThe organic layer was washed 4 times with saturated sodium chloride
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (methylene chloride/methanol)

Sources & evidence

ORD record
ord-72f609c013e9460fb5a6d2f060c762bc
Source dataset
uspto-grants-2013_03
Patent number
US08399464B2

Reaction notes

Loading…