4-Methylmorpholine → HCID 59750942, compound

HRID 748856Notes

Reaction equation

HRID 748856 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]([C:21]2[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=2[F:28])[C:12]2[N:17]=[CH:16][C:15]([C:18](O)=[O:19])=[CH:14][CH:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.CN1CCOCC1.[CH3:36][O:37][NH3+:38].[Cl-].Cl.C(N=C=NCCCN(C)C)C>ClCCl.C(OCC)(=O)C.O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([CH:11]([C:21]2[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=2[F:28])[C:12]2[CH:13]=[CH:14][C:15]([C:18]([NH:38][O:37][CH3:36])=[O:19])=[CH:16][N:17]=2)(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 79724-MethylmorpholineHCID 11639O-methylhydroxylammonium chlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23114724[6-[(4-Chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-3-yl]carboxylic acid

Product 1

HCID 59750942HCID 59750942, compoundYield 52%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of the [6-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-3-yl]carboxylic acid (100 mg, 0.236 mmol), which had been obtained in Example 338, in dichloromethane (6 ml) were added N-methylmorpholine (77.7 μl, 0.708 mmol), o-methylhydroxylamine hydrochloride (23.6 mg, 0.283 mzmol), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (54.3 mg, 0.283 mmol). After stirring at room temperature for 1 hour, tetrahydrofuran (1 ml) was added to the mixture. The reaction mixture was stirred at room temperature for 18 hours. The mixture was then diluted with dichloromethane, and washed with water and brine. The organic layer thus obtained was dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to flash chromatography on a silica gel column and a fraction obtained from the elution portion with hexane:ethyl acetate=1:1 was concentrated, whereby a white solid was obtained. The solid was washed with ethyl acetate, whereby the title compound (55.1 mg, 0.122 mmol, 52%) was obtained as a white powder.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 18 hours
  2. washwashed with water and brine
  3. customThe organic layer thus obtained
  4. dry with materialwas dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customa fraction obtained from the elution portion with hexane
  7. concentrationethyl acetate=1:1 was concentrated
  8. customwhereby a white solid was obtained

Sources & evidence

ORD record
ord-3f202f9915554b798450afdc16e60a93
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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