Ethanolamine → HCID 57736474, compound

HRID 1641686Notes

Reaction equation

HRID 1641686 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])=[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.[NH2:30][CH2:31][CH2:32][OH:33].[OH:34]N1C2C=CC=CC=2N=N1.Cl.[CH2:45]([N:47]=C=NCCCN(C)C)[CH3:46]>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]([F:29])=[CH:25][CH:24]=1)(=[O:22])=[O:21])[C:10]1[C:11]([CH3:19])=[CH:12][C:31]([C:32]([NH:47][CH2:45][CH2:46][OH:34])=[O:33])=[N:30][CH:15]=1

Participants

6

Reactant 4

HCID 700EthanolamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 577364395-[(2,5-Difluorophenyl)[(4-fluorophenyl)sulfonyl]methyl]-4-methylpyridine-2-carboxylic acid

Product 1

HCID 57736474HCID 57736474, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-[(2,5-difluorophenyl)[(4-fluorophenyl)sulfonyl]methyl]-4-methylpyridine-2-carboxylic acid (421 mg, 1.00 mmol) obtained in Example 12 in methylene chloride (10 ml), 2-aminoethanol (0.067 ml, 1.10 mmol), 1-hydroxybenzotriazole (149 mg, 1.10 mmol) 4-methylmorpholine (0.12 ml, 1.10 mmol), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (211 mg, 1.10 mmol) were added at room temperature. After stirring for 7 days at room temperature, the reaction mixture was washed with saturated aqueous sodium hydrogencarbonate. The organic layer was dried over anhydrous sodium sulfate and filtered, then the filtrate was concentrated under reduced pressure, and the resulting residue was subjected to flash silica gel chromatography. The fraction obtained from an elution with hexane:ethyl acetate=2:3 was concentrated under reduced pressure, and the resulting residue was washed with a mixed solvent of ethanol and hexane, and was collected by filtration, to obtain the title compound (427 mg, 0.92 mmol, 92%) as a white solid.

Workup

  1. washthe reaction mixture was washed with saturated aqueous sodium hydrogencarbonate
  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=2:3 was concentrated under reduced pressure
  7. washthe resulting residue was washed with a mixed solvent of ethanol and hexane
  8. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-db8b7f68872b447ba14eedd0b428558e
Source dataset
uspto-grants-2012_02
Patent number
US08114886B2

Reaction notes

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