Pyridine → HCID 57942295, compound

HRID 1898129Notes

Reaction equation

HRID 1898129 reaction equation
[NH2:1][C:2]1C(C#N)=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.Cl[C:12]1[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][C:13]=1[C:22]([F:25])([F:24])[F:23].N1C=CC=C[CH:27]=1.[OH-].[Na+].CC[O:36][C:37]([CH3:39])=[O:38]>>[Cl:8][C:6]1[CH:7]=[C:2]([NH:1][S:18]([C:15]2[CH:16]=[CH:17][C:12]([CH3:27])=[C:13]([C:22]([F:25])([F:24])[F:23])[CH:14]=2)(=[O:20])=[O:19])[C:39]([C:37]([OH:36])=[O:38])=[N:4][CH:5]=1

Participants

6

Reactant 5

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 27807194-Chloro-3-(trifluoromethyl)benzenesulfonyl ChlorideHCID 540742733-Amino-5-chloropyridine-2-carbonitrile

Product 1

HCID 57942295HCID 57942295, compound

Procedure

A 100 mL round-bottom flask was charged with the above 3-amino-2-cyano-5-chloropyridine (8.95 g, 61.54 mmol), 4-chloro-3-trifluoromethyl-benzenesulfonyl chloride (19.6 g, 80 mmol), and pyridine (50 mL). The resultant solution was heated to 60° C. and stirred for overnight. The pyridine was removed in vacuo and dioxane (200 mL) was added, followed by NaOH (28 g, 0.70 mol). The mixture was stirred under reflux for two days. The solvent was subsequently removed in vacuo and ice (100 g) was added and the pH adjusted to 2-3 with conc HCl. The resultant solid was filtered and washed with water twice and was dried in vacuo to afford the light yellow solid. This solid was dissolved in EtOAc and any insoluble solid was filtered off. The filtrate was washed with brine, dried (Na2SO4), filtered and the filtrate was concentrated under reduced pressure to afford 5-chloro-3-(4-methyl-3-trifluoromethyl-benzenesulfonylamino)-pyridine-2-carboxylic acid (16.5 g): (M+H)+ expect 395.0. found 395.0.

Workup

  1. customThe pyridine was removed in vacuo and dioxane (200 mL)
  2. additionwas added
  3. stirringThe mixture was stirred
  4. temperatureunder reflux for two days
  5. customThe solvent was subsequently removed in vacuo and ice (100 g)
  6. additionwas added
  7. filtrationThe resultant solid was filtered
  8. washwashed with water twice
  9. customwas dried in vacuo
  10. customto afford the light yellow solid
  11. filtrationany insoluble solid was filtered off
  12. washThe filtrate was washed with brine
  13. dry with materialdried (Na2SO4)
  14. filtrationfiltered
  15. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-788f598534d0454492b991b7d5d9b066
Source dataset
uspto-grants-2013_08
Patent number
US08519135B2

Reaction notes

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