4-Methylmorpholine → HCID 59750942, compound

HRID 2080422Notes

Reaction equation

HRID 2080422 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.Cl.[CH3:37][O:38][NH2:39].Cl.C(N=C=NCCCN(C)C)C>ClCCl.CCCCCC.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:39][O:38][CH3:37])=[O:19])=[CH:16][N:17]=2)(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 79724-MethylmorpholineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 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 8058HexaneSolvent

Procedure

To a dichloromethane (6 ml) suspension of the [6-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-3-yl]carboxylic acid (100 mg, 0.236 mmol) obtained in Example 50 were added N-methylmorpholine (77.7 μl, 0.708 mmol), O-methylhydroxylamine hydrochloride (23.6 mg, 0.283 mmol), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (54.3 mg, 0.283 mmol). The resulting mixture was stirred at room temperature for 1 hour. To the reaction mixture was added tetrahydrofuran (1 ml). After stirring at room temperature for 18 hours, the reaction mixture was diluted with dichloromethane. The diluted mixture was washed with water and brine. The organic layer thus obtained was dried over magnesium sulfate and concentrated under reduced pressure. The residue thus obtained was subjected to flash silica gel column chromatography. The fraction obtained from the hexane:ethyl acetate=1:1 eluate was concentrated to give a white solid. The resulting solid was washed with ethyl acetate to give the title compound (55.1 mg, 0.122 mmol, 52%) as a white powder.

Workup

  1. stirringAfter stirring at room temperature for 18 hours
  2. washThe diluted mixture was washed with water and brine
  3. customThe organic layer thus obtained
  4. dry with materialwas dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue thus obtained
  7. concentrationethyl acetate=1:1 eluate was concentrated
  8. customto give a white solid
  9. washThe resulting solid was washed with ethyl acetate

Sources & evidence

ORD record
ord-5435eb2fd5c2435da82d3dd0a0896615
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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