Fusaric Acid → 5-Butylpyridine-2-carbonyl chloride
Reaction equation
[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]([OH:13])=O)=[N:9][CH:10]=1)[CH2:2][CH2:3][CH3:4].S(Cl)([Cl:16])=O>>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]([Cl:16])=[O:13])=[N:9][CH:10]=1)[CH2:2][CH2:3][CH3:4]Participants
Procedure
A solution of 5-butylpicolinic acid (1 mL) in thionyl chloride (24 eq.) was heated at 60-70° C. for 1 hour to form 5-butylpicolinoyl chloride. Excess of thionyl chloride was removed. Methyl 2-(5-(4-aminophenyl)thiazole-2-carboxamido)-3-methylbutanoate (Intermediate 2, 200 mg) in DCM (5 mL) and pyridine (5 mL) was added to 5-butylpicolinoyl chloride and the reaction mixture was stirred for 1 hour at RT. Solvent was removed and ether was added to it. The solution was stirred, filtered, washed with water and dried obtain the title compound. 1H NMR (DMSO-d6; 300 MHz): δ 10.81 (s, 1H), 8.57 (d, 1H), 8.60 (s, 1H), 8.41 (s, 1H), 8.12 (m, 3H), 7.92 (d, 1H), 7.81 (d, 2H), 4.35 (t, 1H), 3.68 (s, 3H), 2.75 (t, 2H), 2.28 (m, 1H), 1.64 (m, 2H), 1.37 (m, 2H), 0.97 (m, 9H); MS (ESI) m/z 495.2 [M+H]+.
Sources & evidence
- ORD record
- ord-e379206165964dbdb0fe1f563e79c30b
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08722901B2
Reaction notes
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