Hydrochloric Acid → HCID 58460202, compound

HRID 1946538Notes

Reaction equation

HRID 1946538 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13]3[CH:14]([CH2:18]CC#N)[CH2:15][CH2:16][CH2:17][C:12]=3[N:11]=[C:10]2[CH:22]([CH3:24])[CH3:23])=[CH:4][CH:3]=1.Cl.[C:26]([OH:32])([C:28](F)(F)F)=[O:27]>CO.[OH-].[K+]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][N:9]2[C:13]3[CH:14]([CH2:18][CH2:28][C:26]([OH:32])=[O:27])[CH2:15][CH2:16][CH2:17][C:12]=3[N:11]=[C:10]2[CH:22]([CH3:24])[CH3:23])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 58460237HCID 58460237, compound

Product 1

HCID 58460202HCID 58460202, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14797Potassium HydroxideSolvent3×

Procedure

A solution of Intermediate 78 (128 mg, two batches) in Methanol (3.5 mL) and potassium hydroxide (10M aqueous soln) (0.749 mL) was heated to reflux overnight. LCMS after 18 h indicated approximately 20% conversion to the acid. Further potassium hydroxide (10M aqueous soln) (0.749 mL was added to the reaction mixture and it was left to heat for a further 36 h. LCMS after this time demonstrated full conversion to the acid product. Aqueous HCl (4.85 mL) was added to the reaction mixture to neutralise to the KOH. The product was extracted from the reaction mixture using EtOAc. The organic layer was washed with water, brine and then dried over MgSO4 and filtered, before being concentrated in vacuo to give the product, 88 mg. LC/MS MH+ 361, Rt 2.02 mins (5 min run, TFA modifier).

Workup

  1. temperatureto reflux overnight
  2. waitwas left
  3. temperatureto heat for a further 36 h
  4. extractionThe product was extracted from the reaction mixture
  5. washThe organic layer was washed with water, brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationbefore being concentrated in vacuo
  9. customto give the product, 88 mg

Sources & evidence

ORD record
ord-62fdfc94f8d4429285eb4506c3636d8e
Source dataset
uspto-grants-2013_03
Patent number
US08399444B2

Reaction notes

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