Pyridine → HCID 19349437, compound

HRID 1636805Notes

Reaction equation

HRID 1636805 reaction equation
[C:1]([C:3]([C:6]1[CH:7]=[C:8]([CH:12]=[C:13]([CH2:15][N:16]2[CH:20]=[N:19][CH:18]=[N:17]2)[CH:14]=1)[C:9]([NH2:11])=O)([CH3:5])[CH3:4])#[N:2].N1C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.C(=O)([O-])O.[Na+]>O.O1CCOCC1>[C:1]([C:3]([C:6]1[CH:7]=[C:8]([CH:12]=[C:13]([CH2:15][N:16]2[CH:20]=[N:19][CH:18]=[N:17]2)[CH:14]=1)[C:9]#[N:11])([CH3:5])[CH3:4])#[N:2]

Participants

7

Reactant 4

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 516892Sodium BicarbonateHCID 17992068HCID 17992068, compound

Product 1

HCID 19349437HCID 19349437, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of the product from Example 22 (0.41 g), pyridine (0.25 ml) and 1,4-dioxan (5 ml) was stirred while trifluoroacetic anhydride (0.24 ml) was added dropwise The resulting solution was kept at room temperature for 18 h, diluted with water (10 ml), made basic with sodium hydrogen carbonate and extracted three times with ethyl acetate. The extracts were combined, dried and evaporated to dryness, and the residue was purified by flash column chromatography, eluting with methanol:chloroform (3:97 by volume) to give 3-(1-cyano-1-methylethyl)-5-(1H-1,2,4-triazol-1-ylmethyl)benzonitrile, mp. 90°-92°.

Workup

  1. additionwas added dropwise The resulting solution
  2. extractionextracted three times with ethyl acetate
  3. customdried
  4. customevaporated to dryness
  5. customthe residue was purified by flash column chromatography
  6. washeluting with methanol:chloroform (3:97 by volume)

Sources & evidence

ORD record
ord-9453b3ea0ce8409ebba90eacbf129983
Source dataset
uspto-grants-2000_03
Patent number
USRE036617

Reaction notes

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