Acetic Acid → HCID 21106452, compound

HRID 1765055Notes

Reaction equation

HRID 1765055 reaction equation
COC1C=CC(C[NH:8][C:9]2[CH:14]=[C:13]([N:15]3[CH:19]=[N:18][C:17]([NH:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[N:16]3)[CH:12]=[CH:11][N:10]=2)=CC=1.C(O)(=O)C>C(O)(C(F)(F)F)=O>[C:21]1([NH:20][C:17]2[N:18]=[CH:19][N:15]([C:13]3[CH:12]=[CH:11][N:10]=[C:9]([NH2:8])[CH:14]=3)[N:16]=2)[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 21106455HCID 21106455, compound

Product 1

HCID 21106452HCID 21106452, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

[1.5 g, 4.03 mMol] of (4-Methoxy-benzyl)-[4-(3-phenylamino-[1,2,4]triazol-1-yl)-pyridin-2-yl]-amine was dissolved in 25 mL of TFA and stirred at 40 C. in a sealed tube for 16 hrs. Then, 10 mL of glacial acetic acid was added and the mixture was stirred at 40 C. for an additional 24 hr. The solvent was removed under reduced pressure and the residue triturated with MTBE, The crude material was treated with water and neutralized with 11.4N ammonium hydroxide to pH 9. The resulting solid was isolated via suction filtration and washed with water. This crude product was treated with 0.25N HCl and particulates removed via suction filtration. The filtrates were neutralized with conc. ammonium hydroxide to a pH of 10 and the mixture was extracted with chloroform twice. The organics were combined and washed with water and brine, dried (Na2SO4), and concentrated under reduced pressure. Tan powder collected; 300 mg (33%). 1H NMR 500 MHz (DMSO-d6) ∂ 6.22(s ex, 2H), 6.88(m, 2H), 7.09d, 1H), 7.26(t, 2H), 7.67(d, 2H), 7.97(d, 1H), 9.14(s, 1H), 9.52(s ex, 1H). LC/MS [M+H+]253.

Workup

  1. stirringthe mixture was stirred at 40 C
  2. waitfor an additional 24 hr
  3. customThe solvent was removed under reduced pressure
  4. customthe residue triturated with MTBE
  5. additionThe crude material was treated with water and neutralized with 11.4N ammonium hydroxide to pH 9
  6. customThe resulting solid was isolated via suction filtration
  7. washwashed with water
  8. additionThis crude product was treated with 0.25N HCl and particulates
  9. customremoved via suction filtration
  10. extractionthe mixture was extracted with chloroform twice
  11. washwashed with water and brine
  12. dry with materialdried (Na2SO4)
  13. concentrationconcentrated under reduced pressure
  14. customTan powder collected

Sources & evidence

ORD record
ord-816555dc7ed643bda50c6fabf3adbdf5
Source dataset
uspto-grants-2007_06
Patent number
US07226920B2

Reaction notes

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