Pyridine → HCID 57942185, compound

HRID 1898216Notes

Reaction equation

HRID 1898216 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:9]([C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1)=[O:10].N1C=CC=CC=1.[CH3:23][S:24](Cl)(=[O:26])=[O:25].[OH-].[Na+]>C1COCC1>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][S:24]([CH3:23])(=[O:26])=[O:25])=[C:3]([C:9]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)=[O:10])[CH:4]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 14798Sodium HydroxideHCID 31297Methanesulfonyl chlorideHCID 10214538(2-Amino-5-chlorophenyl)-pyridin-4-yl methanone

Product 1

HCID 57942185HCID 57942185, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 250 mL flask was charged with (2-amino-5-chloro-phenyl)-pyridin-4-yl-methanone (10.0 g, 43.1 mmol) and pyridine (43 mL) under nitrogen. To the resultant solution was added methanesulfonyl chloride (7.06 mL, 90.5 mmol) and the reaction was stirred at room temperature overnight. The following morning, the organics were concentrated in vacuo at 60° C., followed by hydrolysis of the bis-sulfonamide employing THF (65 mL) and sodium hydroxide (65 mL, 4.0 M). The resultant homogeneous solution was stirred at room temperature for 120 min. Upon completion of the hydrolysis, the THF was removed under reduced pressure and the pH of the aqueous layer was adjusted to 5-6 with 6 M HCl. The resultant solution was diluted with EtOAc and the organics were washed with 10% HCl and saturated sodium bicarbonate, dried with sodium sulfate, concentrated in vacuo, and purified via automated silica gel chromatography to generate the desired methanesulfonamide: MS (ES) (M+H)+ expected 311.0. found 311.1.

Workup

  1. concentrationThe following morning, the organics were concentrated in vacuo at 60° C.
  2. customfollowed by hydrolysis of the bis-sulfonamide
  3. stirringThe resultant homogeneous solution was stirred at room temperature for 120 min
  4. customUpon completion of the hydrolysis
  5. customthe THF was removed under reduced pressure
  6. additionThe resultant solution was diluted with EtOAc
  7. washthe organics were washed with 10% HCl and saturated sodium bicarbonate
  8. dry with materialdried with sodium sulfate
  9. concentrationconcentrated in vacuo
  10. custompurified

Sources & evidence

ORD record
ord-21261379afdb4e1095357fe2fe889b53
Source dataset
uspto-grants-2013_08
Patent number
US08519135B2

Reaction notes

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