4-Methylmorpholine → 5-[(2,5-Difluorophenyl)[(4-fluorophenyl)sulfonyl]methyl]-4-methyl-N-[3-(methylthio)propyl]pyridine-2-carboxamide

HRID 1641720Notes

Reaction equation

HRID 1641720 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](O)=[O:17])=[N:14][CH:15]=1.[CH3:30][S:31][CH2:32][CH2:33][CH2:34][NH2:35].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: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]([NH:35][CH2:34][CH2:33][CH2:32][S:31][CH3:30])=[O:17])=[N:14][CH:15]=1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 777433-(Methylthio)propylamineHCID 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 577365375-[(2,5-Difluorophenyl)[(4-fluorophenyl)sulfonyl]methyl]-4-methyl-N-[3-(methylthio)propyl]pyridine-2-carboxamideYield 94.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-[(2,5-difluorophenyl)[(4-fluorophenyl)sulfonyl]methyl]-4-methylpyridine-2-carboxylic acid (222 mg, 0.527 mmol) obtained in Example 12 in methylene chloride (5 ml), 3-methylthiopropylamine (66 mg, 0.632 mmol), 1-hydroxybenzotriazole (71 mg, 0.527 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (121 mg, 0.632 mmol) and 4-methylmorpholine (69 μl, 0.632 mmol) were added. The reaction solution was stirred for 3 days at room temperature, and was concentrated under reduced pressure. The concentration residue was subjected to silica gel column chromatography, and the fraction obtained from an elution with ethyl acetate:methylene chloride (=1:20) was concentrated under reduced pressure, to obtain the title compound (253 mg, 0.497 mmol, 94%) as a white solid.

Workup

  1. concentrationwas concentrated under reduced pressure
  2. customthe fraction obtained from an elution with ethyl acetate
  3. concentrationmethylene chloride (=1:20) was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5ed0a925550b41b0af54ea47b23a0de8
Source dataset
uspto-grants-2012_02
Patent number
US08114886B2

Reaction notes

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