Sulfuric Acid → 4-[2-Ethyl-4-(4-fluorophenyl)-1,3-thiazol-5-YL]-2-pyridylamine

HRID 1496635Notes

Reaction equation

HRID 1496635 reaction equation
S(=O)(=O)(O)O.C([NH:13][C:14]1[CH:19]=[C:18]([C:20]2[S:24][C:23]([CH2:25][CH3:26])=[N:22][C:21]=2[C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)[CH:17]=[CH:16][N:15]=1)C1C=CC=CC=1.[OH-].[Na+]>>[CH2:25]([C:23]1[S:24][C:20]([C:18]2[CH:17]=[CH:16][N:15]=[C:14]([NH2:13])[CH:19]=2)=[C:21]([C:27]2[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=2)[N:22]=1)[CH3:26]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 67537630N-benzyl-4-[2-ethyl-4-(4-fluorophenyl)-1,3-thiazol-5-yl]pyridine-2-amine

Product 1

HCID 115584724-[2-Ethyl-4-(4-fluorophenyl)-1,3-thiazol-5-YL]-2-pyridylamine

Procedure

With ice cooling, 23 ml of conc. sulphuric acid are added to 4.75 g (10.9 mmol) of N-benzyl-4-[2-ethyl-4-(4-fluorophenyl)-1,3-thiazol-5-yl]pyridine-2-amine, and the reaction mixture is stirred at room temperature for 30 min. The reaction mixture is stirred into 100 ml of ice-water, the pH is adjusted to 10 using concentrated aqueous sodium hydroxide solution and the mixture is extracted with dichloromethane (3×100 ml). The combined organic phases are dried over MgSO4 and freed from the solvent under reduced pressure. The residue is triturated with MTBE and filtered off. The product obtained is 2.80 g (82%) of a beige solid; log P (pH2.7): 1.29 with MS (ESI): 300.1 ([M+H]+).

Workup

  1. extractionthe mixture is extracted with dichloromethane (3×100 ml)
  2. dry with materialThe combined organic phases are dried over MgSO4
  3. customThe residue is triturated with MTBE
  4. filtrationfiltered off
  5. customThe product obtained

Sources & evidence

ORD record
ord-210e112c9e3943e5a593e0ca7177feb1
Source dataset
uspto-grants-2015_12
Patent number
US09198426B2

Reaction notes

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