4-Methylmorpholine → HCID 57736410, compound

HRID 1641725Notes

Reaction equation

HRID 1641725 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:13]([C:16]([OH:18])=O)=[N:14][CH:15]=1.Cl.[CH3:31][O:32][NH2:33].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.CN1CCOCC1>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:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=1)(=[O:22])=[O:21])[C:10]1[C:11]([CH3:19])=[CH:12][C:13]([C:16]([NH:33][O:32][CH3:31])=[O:18])=[N:14][CH:15]=1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 521874O-Methylhydroxylamine hydrochlorideHCID 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 57736410HCID 57736410, compoundYield 64.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-[(2,5-difluorophenyl)[(4-fluorophenyl)sulfonyl]methyl]-4-methylpyridine-2-carboxylic acid (96 mg, 0.228 mmol) obtained in Example 12 in methylene chloride (3 ml), O-methylhydroxyamine hydrochloride (23 mg, 0.273 mmol), 1-hydroxybenzotriazole (31 mg, 0.228 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (52 mg, 0.273 mmol) and 4-methylmorpholine (59 μl, 0.546 mmol) were added. The reaction solution was stirred for 5 days at room temperature, and was concentrated under reduced pressure. The resulting concentration residue was subjected to silica gel column chromatography, and the fraction obtained from an elution with 65% ethyl acetate/hexane was concentrated under reduced pressure to obtain a white solid. The resulting solid was washed with ethylacetate-hexane, and then was collected by filtration, to obtain the title compound (66 mg, 0.147 mmol, 64%) as a white powder.

Workup

  1. concentrationwas concentrated under reduced pressure
  2. concentrationThe resulting concentration residue
  3. customthe fraction obtained from an elution with 65% ethyl acetate/hexane
  4. concentrationwas concentrated under reduced pressure
  5. customto obtain a white solid
  6. washThe resulting solid was washed with ethylacetate-hexane
  7. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-30ff5762cdf44ccf9108ad8fc105d75a
Source dataset
uspto-grants-2012_02
Patent number
US08114886B2

Reaction notes

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