Ethanolamine → HCID 57736426, compound

HRID 1641719Notes

Reaction equation

HRID 1641719 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH:9]([S:20]([C:23]1[CH:28]=[CH:27][C:26]([F:29])=[C:25]([CH3:30])[CH:24]=1)(=[O:22])=[O:21])[C:10]1[C:11]([CH3:19])=[CH:12][C:13]([C:16]([OH:18])=O)=[N:14][CH:15]=1.[NH2:31][CH2:32][CH2:33][OH:34].Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>C(Cl)Cl.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH:9]([S:20]([C:23]1[CH:28]=[CH:27][C:26]([F:29])=[C:25]([CH3:30])[CH:24]=1)(=[O:21])=[O:22])[C:10]1[C:11]([CH3:19])=[CH:12][C:13]([C:16]([NH:31][CH2:32][CH2:33][OH:34])=[O:18])=[N:14][CH:15]=1

Participants

8

Reactant 5

HCID 700EthanolamineHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57736418HCID 57736418, compound

Product 1

HCID 57736426HCID 57736426, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

5-[(2,5-Difluorophenyl)[(4-fluoro-3-methylphenyl)sulfonyl]methyl]-4-methylpyridine-2-carboxylic acid (300 mg, 0.69 mmol), 2-aminoethanol (60 μl, 1.0 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (193 mg, 1.0 mmol), 1-hydroxybenzotriazole (93 mg, 0.69 mmol), and triethylamine (292 μl, 2.1 mmol) were dissolved in methylene chloride (60 ml), and the solution was stirred overnight at room temperature. Water was added to the reaction mixture, and the mixture was extracted twice with methylene chloride. The combined organic layer was dried over anhydrous sodium sulfate and filtered, and then the filtrate was concentrated under reduced pressure. The resulting residue was purified by preparative thin-layer chromatography (developed with 5% methanol/methylene chloride, eluted with 30% methanol/methylene chloride), to obtain the title compound (190 mg, 0.39 mmol, 58%) as a white amorphous substance.

Workup

  1. extractionthe mixture was extracted twice with methylene chloride
  2. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe resulting residue was purified by preparative thin-layer chromatography (developed with 5% methanol/methylene chloride, eluted with 30% methanol/methylene chloride)

Sources & evidence

ORD record
ord-53090260c9484112a411c2da6f4d9bf6
Source dataset
uspto-grants-2012_02
Patent number
US08114886B2

Reaction notes

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