4-Methylmorpholine → 5-[[(4-Fluorophenyl)thio](2,3,6-trifluorophenyl)methyl]-N,N,4-trimethylpyridine-2-carboxamide

HRID 1641700Notes

Reaction equation

HRID 1641700 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH:9]([C:20]2[C:25]([F:26])=[CH:24][CH:23]=[C:22]([F:27])[C:21]=2[F:28])[C:10]2[C:11]([CH3:19])=[CH:12][C:13]([C:16](O)=[O:17])=[N:14][CH:15]=2)=[CH:4][CH:3]=1.Cl.[CH3:30][NH:31][CH3:32].ON1C2C=CC=CC=2N=N1.CN1CCOCC1.Cl.C(N=C=NCCCN(C)C)C>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][CH:9]([C:20]2[C:25]([F:26])=[CH:24][CH:23]=[C:22]([F:27])[C:21]=2[F:28])[C:10]2[C:11]([CH3:19])=[CH:12][C:13]([C:16]([N:31]([CH3:32])[CH3:30])=[O:17])=[N:14][CH:15]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 10473Dimethylamine, hydrochlorideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 577364725-[[(4-Fluorophenyl)thio](2,3,6-trifluorophenyl)methyl]-4-methylpyridine-2-carboxylic Acid

Product 1

HCID 577364645-[[(4-Fluorophenyl)thio](2,3,6-trifluorophenyl)methyl]-N,N,4-trimethylpyridine-2-carboxamideYield 91.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-[[(4-fluorophenyl)thio](2,3,6-trifluorophenyl)methyl]-4-m ethylpyridine-2-carboxylic acid (383 mg, 0.94 mmol) in methylene chloride (10 ml), dimethylamine hydrochloride (85 mg, 1.03 mmol), 1-hydroxybenzotriazole (140 mg, 1.03 mmol), 4-methylmorpholine (0.227 ml, 2.07 mmol), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (198 mg, 1.03 mmol) were added at room temperature. After stirring for 17 hours at room temperature, the reaction mixture was washed with 0.5 N hydrochloric acid. The organic layer was dried over anhydrous sodium sulfate and filtered, then the filtrate was concentrated under reduced pressure, and the resulting residue was subjected to flash silica gel chromatography. The fraction obtained from an elution with hexane:ethyl acetate=1:1 was concentrated under reduced pressure to obtain the title compound (373 mg, 0.86 mmol, 91%) as a white solid.

Workup

  1. washthe reaction mixture was washed with 0.5 N hydrochloric acid
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe fraction obtained from an elution with hexane
  6. concentrationethyl acetate=1:1 was concentrated under reduced pressure

Sources & evidence

ORD record
ord-82da8c52249840459b87f6ada31349a3
Source dataset
uspto-grants-2012_02
Patent number
US08114886B2

Reaction notes

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