Pyridine → HCID 19349437, compound

HRID 2107767Notes

Reaction equation

HRID 2107767 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-0e26dab784b24dee8584d7c011c3f58f
Source dataset
uspto-grants-1990_06
Patent number
US04935437

Reaction notes

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