Pyridine → HCID 10342851, compound

HRID 465596Notes

Reaction equation

HRID 465596 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]([CH2:22][CH2:23][CH2:24][C:25]2[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=2)[CH2:17][CH2:18][C:19]([NH2:21])=O)(=[O:10])=[O:9])=[CH:4][CH:3]=1.N1C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>O1CCOCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]([CH2:22][CH2:23][CH2:24][C:25]2[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=2)[CH2:17][CH2:18][C:19]#[N:21])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 10072535HCID 10072535, compound

Product 1

HCID 10342851HCID 10342851, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 1.44 g of 8-(p-chlorophenylsulfonamido)-4-[3-(3-pyridyl)propyl]-octanamide (example 24) and 0.52 ml pyridine in 5.8 ml dioxane is cooled to 0° and 0.51 ml trifluoroacetic anhydride is added over a period of 1 h. The mixture is then stirred at room temperature for 3 h. The reaction is quenched by the addition of saturated aqueous sodium bicarbonate solution and extracted with methylene chloride (2×20 ml). The combined organic extracts are dried, filtered and evaporated to give 8-(p-chlorophenylsulfonamido)-4-[3-(3-pyridyl)propyl]-octanenitrile.

Workup

  1. temperatureis cooled to 0°
  2. customThe reaction is quenched by the addition of saturated aqueous sodium bicarbonate solution
  3. extractionextracted with methylene chloride (2×20 ml)
  4. customThe combined organic extracts are dried
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-ab80968b1f2548629422f5c1222fdb93
Source dataset
uspto-grants-1992_10
Patent number
US05153214

Reaction notes

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