Dichloromethane → HCID 136159955, compound

HRID 1947222Notes

Reaction equation

HRID 1947222 reaction equation
C([O:8][C:9]1[CH:14]=[C:13]([O:15]CC2C=CC=CC=2)[C:12]([CH:23]([CH3:25])[CH3:24])=[CH:11][C:10]=1[C:26]1[N:27]([N:32]2[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)[C:28](=S)[NH:29][N:30]=1)C1C=CC=CC=1.C(Cl)Cl.B(Cl)(Cl)Cl.C(=O)([O-])[OH:46].[Na+]>CO>[OH:8][C:9]1[CH:14]=[C:13]([OH:15])[C:12]([CH:23]([CH3:25])[CH3:24])=[CH:11][C:10]=1[C:26]1[N:27]([N:32]2[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]2)[C:28](=[O:46])[NH:29][N:30]=1

Participants

6

Reactant 4

HCID 6344Dichloromethane2×HCID 25135Boron TrichlorideHCID 516892Sodium BicarbonateHCID 86624313HCID 86624313, compound

Product 1

HCID 136159955HCID 136159955, compoundYield 16.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-(2,4-bis-benzyloxy-5-isopropyl-phenyl)-4-piperidin-1-yl-2,4-dihydro-[1,2,4]triazol-3-thione (F67-05: 92 mg, 0.18 mmol), methylene chloride (2 mL) and a methylene chloride solution of boron trichloride (1 mol/L, 1 mL) were placed in a test tube and stirred at room temperature for 1 hour. After completing the reaction, methanol and sodium hydrogencarbonate were added to the reaction mixture and solids were separated by filtration. The mother liquor thus obtained was concentrated under reduced pressure and the residue was purified by HPLC fractionation to obtain the title compound (OH-a24 trifluoroacetate, 9.5 mg, 16.6%).

Workup

  1. additionwere added to the reaction mixture and solids
  2. customwere separated by filtration
  3. customThe mother liquor thus obtained
  4. concentrationwas concentrated under reduced pressure
  5. customthe residue was purified by HPLC fractionation

Sources & evidence

ORD record
ord-962c02f0830241a2bf12d7c88c7f1db2
Source dataset
uspto-grants-2013_03
Patent number
US08399464B2

Reaction notes

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