Picolinoyl Chloride Hydrochloride → N-(5-Bromo-4-(trifluoromethyl)thiazol-2-yl)picolinamide

HRID 716621Notes

Reaction equation

HRID 716621 reaction equation
[Br:1][C:2]1[S:6][C:5]([NH2:7])=[N:4][C:3]=1[C:8]([F:11])([F:10])[F:9].Cl.[N:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19](Cl)=[O:20]>C(Cl)Cl>[Br:1][C:2]1[S:6][C:5]([NH:7][C:19](=[O:20])[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][N:13]=2)=[N:4][C:3]=1[C:8]([F:11])([F:10])[F:9]

Participants

4

Reactant 2

HCID 135033Picolinoyl Chloride HydrochlorideHCID 157107015-Bromo-4-(trifluoromethyl)-1,3-thiazol-2-amine

Product 1

HCID 86688229N-(5-Bromo-4-(trifluoromethyl)thiazol-2-yl)picolinamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 5-bromo-4-(trifluoromethyl)thiazol-2-amine (0.204 g, 0.826 mmol) ethyldiisopropylamine (0.36 mL, 2.1 mmol) in methylene chloride (4 mL) at 0° C. was added picolinoyl chloride hydrochloride (0.162 g, 0.908 mmol) and the reaction mixture was stirred at room temperature for 15 h. The reaction mixture was diluted with methylene chloride and washed with saturated NaHCO3, dried, filtered and concentrated under vacuum to give the crude product. The residue was purified by column chromatography eluting with ethyl acetate/hexanes 0 to 30% to give the product.

Workup

  1. washwashed with saturated NaHCO3
  2. customdried
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-c2f87ae475744f28b6b9d3053afc284e
Source dataset
uspto-grants-2015_11
Patent number
US09192603B2

Reaction notes

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