Hydrochloric Acid → HCID 71230879, compound

HRID 2172681Notes

Reaction equation

HRID 2172681 reaction equation
C[O:2][C:3](=[O:20])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[O:13][N:12]=2)=[CH:7][CH:6]=1.Cl>C1COCC1>[F:18][C:16]([F:17])([F:19])[C:14]1[O:13][N:12]=[C:11]([C:8]2[CH:7]=[CH:6][C:5]([CH2:4][C:3]([OH:20])=[O:2])=[CH:10][CH:9]=2)[N:15]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 71230921HCID 71230921, compound

Product 1

HCID 71230879HCID 71230879, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

[4-(5-Trifluoromethyl-[1,2,4]oxadiazol-3-yl)-phenyl]-acetic acid methyl ester (1.333 g, 4.66 mmol) was dissolved in THF (8.28 mL) and 4 M HCl (12.42 mL) added. The mixture was stirred at RT for 24 h. The reaction mixture was then stirred for 29 h at 60° C. The solvent was removed by rotary evaporation. To ensure complete removal of the HCl, the product was dissolved in Toluene and evaporated again 3 times. The substance was then dissolved in water:acetonitrile 1:1 and lyophilised over the weekend. For analytical purposes, a small sample was subjected to purification by reverse phase prep-HPLC (gradient elution, water/ACN both containing 0.1% TFA). Fractions containing the desired compound were combined and freeze-dried to yield the product as white salt.

Workup

  1. stirringThe reaction mixture was then stirred for 29 h at 60° C
  2. customThe solvent was removed by rotary evaporation
  3. customremoval of the HCl
  4. dissolutionthe product was dissolved in Toluene
  5. customevaporated again 3 times
  6. dissolutionThe substance was then dissolved in water:acetonitrile 1:1
  7. customFor analytical purposes, a small sample was subjected to purification by reverse phase prep-HPLC (
  8. washgradient elution, water/ACN both containing 0.1% TFA)
  9. additionFractions containing the desired compound
  10. customfreeze-dried
  11. customto yield the product as white salt

Sources & evidence

ORD record
ord-3c2b83e7c0454a3eaa54f0d8f3dd1172
Source dataset
uspto-grants-2015_06
Patent number
US09056843B2

Reaction notes

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