Ethanolamine → HCID 57736482, compound

HRID 1641706Notes

Reaction equation

HRID 1641706 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])=[C:25]([F:31])[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.[NH2:32][CH2:33][CH2:34][OH:35].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]([F:8])=[CH:4][C:3]=1[CH:9]([S:20]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([F:31])[CH:24]=1)(=[O:21])=[O:22])[C:10]1[C:11]([CH3:19])=[CH:12][C:13]([C:16]([NH:32][CH2:33][CH2:34][OH:35])=[O:18])=[N:14][CH:15]=1

Participants

7

Reactant 5

HCID 700EthanolamineHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57736406HCID 57736406, compound

Product 1

HCID 57736482HCID 57736482, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-[(2,5-difluorophenyl)[(3-fluoro-4-methoxyphenyl)sulfonyl]methyl]-4-methylpyridine-2-carboxylic acid (113 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 (0.030 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 19 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 ethyl acetate was concentrated under reduced pressure, and the resulting residue was washed with a mixed solvent of ethanol and diethyl ether, and was collected by filtration, to obtain the title compound (99 mg, 0.20 mmol, 80%) 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 ethyl acetate
  6. concentrationwas 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-112daa28d659467e9e5f65003698d592
Source dataset
uspto-grants-2012_02
Patent number
US08114886B2

Reaction notes

Loading…