Hydrochloric Acid → HCID 178433850, compound

HRID 628422Notes

Reaction equation

HRID 628422 reaction equation
[CH3:1][C:2]1[N:6]2[C:7]3[CH:13]=[C:12]([C:14]4[CH:18]=[CH:17][NH:16][N:15]=4)[N:11]([CH2:19][C:20]4[CH:21]=C([CH:25]=[CH:26][CH:27]=4)C#N)[C:8]=3[CH:9]=[CH:10][C:5]2=[N:4][N:3]=1.[OH-:28].[K+].[Na+].[Cl-].Cl.[CH3:33][CH2:34][OH:35]>C(Cl)(Cl)Cl.CC(O)C>[CH3:1][C:2]1[N:6]2[C:7]3[CH:13]=[C:12]([C:14]4[CH:18]=[CH:17][NH:16][N:15]=4)[N:11]([CH2:19][C:20]4[CH:21]=[C:33]([CH:25]=[CH:26][CH:27]=4)[C:34]([OH:28])=[O:35])[C:8]=3[CH:9]=[CH:10][C:5]2=[N:4][N:3]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 5234Sodium ChlorideHCID 14797Potassium HydroxideHCID 178433848HCID 178433848, compound

Product 1

HCID 178433850HCID 178433850, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6212ChloroformSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-{[1-methyl-7-(1H-pyrazol-3-yl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridin-6-yl]methyl}benzonitrile (0.29 g, 0.82 mmol, from Step 4) and KOH (0.46 g, 8.2 mmol) in EtOH (29 mL) was heated at 80° C. overnight in a sealed tube. Thereafter, the reaction was heated at 120-135° C. for 37 hours. Solvent was removed in vacuo. The reaction mixture was diluted with water, and the pH was adjusted to pH 4 by the addition of 1 N HCl. The brown solid that formed was isolated by filtration. The filtrate was saturated with solid NaCl, the pH was lowered to pH 3 by the addition of 1 N HCl and additional product was obtained by extraction with five portions of 10% iPrOH in CHCl3. The extract was dried over sodium sulfate, filtered and concentrated. The solid obtained was combined with the solid that was isolated by filtration above. The 0.4 g of material containing crude product was used without further purification in Step 6.

Workup

  1. temperatureThereafter, the reaction was heated at 120-135° C. for 37 hours
  2. customSolvent was removed in vacuo
  3. additionThe reaction mixture was diluted with water
  4. additionthe pH was adjusted to pH 4 by the addition of 1 N HCl
  5. customThe brown solid that formed
  6. customwas isolated by filtration
  7. dry with materialThe extract was dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe solid obtained
  11. customthat was isolated by filtration above
  12. customwas used without further purification in Step 6

Sources & evidence

ORD record
ord-6a484c5489b9406dad9e83c0f141ebcc
Source dataset
uspto-grants-2016_04
Patent number
US09309246B2

Reaction notes

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