Ethanolamine → HCID 57736516, compound

HRID 1641717Notes

Reaction equation

HRID 1641717 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]([C:22]2[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:23]=2[F:29])[C:12]2[C:13]([CH3:21])=[CH:14][C:15]([C:18](O)=[O:19])=[N:16][CH:17]=2)(=[O:10])=[O:9])=[CH:4][C:3]=1[CH3:30].[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>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]([C:22]2[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:23]=2[F:29])[C:12]2[C:13]([CH3:21])=[CH:14][C:15]([C:18]([NH:31][CH2:32][CH2:33][OH:34])=[O:19])=[N:16][CH:17]=2)(=[O:10])=[O:9])=[CH:4][C:3]=1[CH3:30]

Participants

8

Reactant 5

HCID 700EthanolamineHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57736510HCID 57736510, compound

Product 1

HCID 57736516HCID 57736516, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

5-[[(4-Chloro-3-methylphenyl)sulfonyl](2,5-difluorophenyl) methyl]-4-methylpyridine-2-carboxylic acid (300 mg, 0.66 mmol), 2-aminoethanol (60 μl, 0.99 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (191 mg, 0.99 mmol), 1-hydroxybenzotriazole (89 mg, 0.66 mmol), and triethylamine (275 μl, 1.98 mmol) were dissolved in methylene chloride (60 ml), and the resulting mixture 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, 0.38 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-f8abea73789c41f290d4f4bc430db598
Source dataset
uspto-grants-2012_02
Patent number
US08114886B2

Reaction notes

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