Pyridine → HCID 10342851, compound

HRID 1494136Notes

Reaction equation

HRID 1494136 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH:12]([CH2:16][CH:17]([CH2:22][CH2:23][CH2:24][C:25]2[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=2)CCCC)C(N)=O)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[N:31]1C=C[CH:34]=[CH:33][CH:32]=1.F[C:38](F)(F)[C:39](OC(=O)C(F)(F)F)=O>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([NH:11][CH2:12][CH2:16][CH2:17][CH2:22][CH:23]([CH2:24][CH2:25][CH2:30][C:29]2[CH:28]=[N:27][CH:26]=[CH:38][CH:39]=2)[CH2:34][CH2:33][C:32]#[N:31])(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 86744863HCID 86744863, compound

Product 1

HCID 10342851HCID 10342851, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 1.44 g of 8-(p-chlorophenylsulfonamido-4-[3-(3-pyridyl)-propyl]-octanamide and 0.52 mL pyridine in 5.8 mL dioxane is cooled to 0° C. and 0.51 mL trifluoroacetic anhydride is added over a period of 1 hour. The mixture is then stirred at room temperature for 3 hours. 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-chlorophenyl- sulfonamido)-4-[3-(3-pyridyl)propyl]octanenitrile.

Workup

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

Sources & evidence

ORD record
ord-a30b9d772ad84bc7b58c937cad95486f
Source dataset
uspto-grants-1991_06
Patent number
US05025025

Reaction notes

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