Ethanolamine → HCID 57736445, compound

HRID 1641705Notes

Reaction equation

HRID 1641705 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]([O:29][CH3:30])=[CH:25][CH:24]=1)(=[O:22])=[O:21])[C:10]1[C:11]([CH3:19])=[CH:12]C(C(O)=O)=N[CH:15]=1.[NH2:31][CH2:32][CH2:33][OH:34].ON1C2C=CC=CC=2N=N1.C[N:46]1CC[O:49][CH2:48][CH2:47]1.Cl.C(N=C=NCCCN(C)C)C>C(Cl)Cl>[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]([O:29][CH3:30])=[CH:25][CH:24]=1)(=[O:21])=[O:22])[C:10]1[C:11]([CH3:19])=[CH:12][C:32]([C:33]([NH:46][CH2:47][CH2:48][OH:49])=[O:34])=[N:31][CH:15]=1

Participants

7

Reactant 5

HCID 700EthanolamineHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57736514HCID 57736514, compound

Product 1

HCID 57736445HCID 57736445, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-[(2,5-difluorophenyl)[(4-methoxyphenyl)sulfonyl]methyl]-4-methylpyridine-2-carboxylic acid (108 mg, 0.25 mmol) in methylene chloride (3 ml), 2-aminoethanol (0.017 ml, 0.28 mmol), 1-hydroxybenzotriazole (37 mg, 0.28 mmol), 4-methylmorpholine (0.0.0 ml, 0.28 mmol), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (53 mg, 0.28 mmol) were added at room temperature. After stirring for 17 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=1:4 was concentrated under reduced pressure, and the resulting residue was washed with a mixed solvent of ethanol and diethyl ether, and then was collected by filtration, to obtain the title compound (96 mg, 0.20 mmol, 81%) as a white solid.

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=1:4 was concentrated under reduced pressure
  7. washthe resulting residue was washed with a mixed solvent of ethanol and diethyl ether
  8. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-d28498da09634fb88501fcca56e6603a
Source dataset
uspto-grants-2012_02
Patent number
US08114886B2

Reaction notes

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