Ethanolamine → HCID 57736438, compound

HRID 1641715Notes

Reaction equation

HRID 1641715 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]([CH3:29])=[CH:25][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.[NH2:30][CH2:31][CH2:32][OH:33].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:24]=[CH:25][C:26]([CH3:29])=[CH:27][CH:28]=1)(=[O:21])=[O:22])[C:10]1[C:11]([CH3:19])=[CH:12][C:13]([C:16]([NH:30][CH2:31][CH2:32][OH:33])=[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 57736476HCID 57736476, compound

Product 1

HCID 57736438HCID 57736438, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

5-[(2,5-Difluorophenyl)[(4-methylphenyl)sulfonyl]meth yl]-4-methylpyridine-2-carboxylic acid (208 mg, 0.5 mmol), 2-aminoethanol (46 μl, 0.75 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride mg, 0.75 mmol), 1-hydroxybenzotriazole (68 mg, 0.5 mmol), and triethylamine (209 μl, 1.5 mmol) were dissolved in methylene chloride (35 ml), and the resulting solution was stirred overnight at room temperature. Water was added to the reaction mixture, and the resulting 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 6% methanol/methylene chloride, eluted with 30% methanol/methylene chloride), to obtain the title compound (125 mg, 0.27 mmol, 54%) as a white amorphous substance.

Workup

  1. extractionthe resulting 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 6% methanol/methylene chloride, eluted with 30% methanol/methylene chloride)

Sources & evidence

ORD record
ord-6b014b6db31a4519a45e8ef173897828
Source dataset
uspto-grants-2012_02
Patent number
US08114886B2

Reaction notes

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