Hydrochloric Acid → HCID 178438834, compound

HRID 1947191Notes

Reaction equation

HRID 1947191 reaction equation
COC[O:4][C:5]1[C:10]([CH:11]([CH3:13])[CH3:12])=[CH:9][C:8]([C:14]2[N:18]([C:19]3[CH:24]=[CH:23][C:22]([N:25]4[CH2:30][CH2:29][O:28][CH2:27][CH2:26]4)=[CH:21][CH:20]=3)[C:17]([OH:31])=[N:16][N:15]=2)=[C:7]([O:32]COC)[CH:6]=1.Cl>C(O)C>[OH:31][C:17]1[N:18]([C:19]2[CH:20]=[CH:21][C:22]([N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)=[CH:23][CH:24]=2)[C:14]([C:8]2[CH:9]=[C:10]([CH:11]([CH3:13])[CH3:12])[C:5]([OH:4])=[CH:6][C:7]=2[OH:32])=[N:15][N:16]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178498575HCID 178498575, compound

Product 1

HCID 178438834HCID 178438834, compoundYield 22.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

An ethanol solution (2 mL) of 1,3-bis(methoxymethoxy)-4-{5-hydroxy-4-[4-(morpholin-4-yl)-phenyl]-4H-[1,2,4]triazol-3-yl}-6-isopropylbenzene (IM6-O-a01: 16.3 mg, 0.034 mmol) was mixed with 5 N hydrochloric acid (1 mL) and reacted at room temperature for 4 hours. The solvent was distilled off under reduced pressure, and the residue was neutralized with 5% sodium hydrogencarbonate and extracted with dichloromethane (30 mL). The extract was dried over anhydrous sodium sulfate. Sodium sulfate was removed by filtration, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (dichloromethane: methanol=30:1-20:1) to obtain the title compound (OH-a01: white solid, 3.0 mg, 22%).

Workup

  1. customreacted at room temperature for 4 hours
  2. distillationThe solvent was distilled off under reduced pressure
  3. extractionextracted with dichloromethane (30 mL)
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. customSodium sulfate was removed by filtration
  6. distillationthe solvent was distilled off under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (dichloromethane: methanol=30:1-20:1)

Sources & evidence

ORD record
ord-5fada7ee77f64c519366d94336ec5810
Source dataset
uspto-grants-2013_03
Patent number
US08399464B2

Reaction notes

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