4-Methylmorpholine → HCID 57736436, compound

HRID 1641726Notes

Reaction equation

HRID 1641726 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.[OH:30][N:31]1[C:35]2C=CC=CC=2N=N1.Cl.[CH2:41](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: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]([N:31]([O:30][CH3:41])[CH3:35])=[O:18])=[N:14][CH:15]=1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 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 57736436HCID 57736436, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-[(2,5-difluorophenyl) [(4-fluorophenyl)sulfonyl]methyl]-4-methylpyridine-2-carboxylic acid (99 mg, 0.235 mmol) obtained in Example 12 in methylene chloride (3 ml), N, O-dimethylhydroxyamine hydrochloride (28 mg, 0.282 mmol), 1-hydroxybenzotriazole (32 mg, 0.235 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride mg, 0.382 mmol) and 4-methylmorpholine (61 μl, 0.564 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 hexane:ethylacetate (=1:1) was concentrated under reduced pressure. Ethyl acetate-hexane was added to the resulting concentration residue, and the solid thus precipitated was collected by filtration, to obtain the title compound (73 mg, 0.157 mmol, 67%) as a white powder.

Workup

  1. concentrationwas concentrated under reduced pressure
  2. concentrationThe resulting concentration residue
  3. customthe fraction obtained from an elution with hexane
  4. concentrationethylacetate (=1:1) was concentrated under reduced pressure
  5. additionEthyl acetate-hexane was added to the resulting concentration residue
  6. customthe solid thus precipitated
  7. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-c01bd78fe3494a2c881e88a9346eaae0
Source dataset
uspto-grants-2012_02
Patent number
US08114886B2

Reaction notes

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