Ethanolamine → 5-[[(4-Fluorophenyl)thio](2,3,6-trifluorophenyl)methyl]-N-(2-hydroxyethyl)-4-methylpyridine-2-carboxamide

HRID 1641737Notes

Reaction equation

HRID 1641737 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.[NH2:29][CH2:30][CH2:31][OH:32].ON1C2C=CC=CC=2N=N1.CN1CCOCC1.Cl.C(N=C=NCCCN(C)C)C>C(Cl)Cl>[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]([NH:29][CH2:30][CH2:31][OH:32])=[O:17])=[N:14][CH:15]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 700EthanolamineHCID 79724-MethylmorpholineHCID 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 577364785-[[(4-Fluorophenyl)thio](2,3,6-trifluorophenyl)methyl]-N-(2-hydroxyethyl)-4-methylpyridine-2-carboxamideYield 97.5%

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 (163 mg, 0.40 mmol) obtained in Example 34 in methylene chloride (5 ml), 2-aminoethanol (0.027 ml, 0.44 mmol), 1-hydroxybenzotriazole (60 mg, 0.44 mmol), 4-methylmorpholine (0.048 ml, 0.44 mmol), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (84 mg, 0.44 mmol) were added at room temperature. After stirring for 3 hours at room temperature, the reaction mixture was washed with water and then with saturated brine. The organic layer was dried over anhydrous sodium sulfate and filtered, then the filtrate was concentrated under reduced pressure, and the obtained residue was subjected to flash silica gel chromatography. The fraction obtained from an elution with hexane:ethyl acetate=2:3 was concentrated under reduced pressure to obtain the title compound (175 mg, 0.39 mmol, 97%) as a colorless oily substance.

Workup

  1. washthe reaction mixture was washed with water
  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=2:3 was concentrated under reduced pressure

Sources & evidence

ORD record
ord-70d3a316d16f492db24b2072dd0413cb
Source dataset
uspto-grants-2012_02
Patent number
US08114886B2

Reaction notes

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