4-Methylmorpholine → 2-(4-Cyclopropanesulfonyl-phenyl)-2-(2,4-difluoro-phenoxy)-N-(5-methoxy-thiazol-2-yl)-acetamide

HRID 1889193Notes

Reaction equation

HRID 1889193 reaction equation
[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([O:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=3[F:25])[C:14](O)=[O:15])=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.[CH3:26][O:27][C:28]1[S:32][C:31]([NH2:33])=[N:30][CH:29]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.CN1CCOCC1>CN(C=O)C.O.C(Cl)Cl>[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([O:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=3[F:25])[C:14]([NH:33][C:31]3[S:32][C:28]([O:27][CH3:26])=[CH:29][N:30]=3)=[O:15])=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:2][CH2:3]1

Participants

9

Reactant 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 203162835-Methoxy-1,3-thiazol-2-amineHCID 596100322-(4-Cyclopropylsulfonylphenyl)-2-(2,4-difluorophenoxy)acetic acid

Product 1

HCID 596100652-(4-Cyclopropanesulfonyl-phenyl)-2-(2,4-difluoro-phenoxy)-N-(5-methoxy-thiazol-2-yl)-acetamideYield 34.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-(4-cyclopropanesulfonylphenyl)-2-(2,4-difluorophenoxy)acetic acid (0.1 g, 0.27 mmol), 5-methoxy-thiazol-2-ylamine (0.042 g, 0.33 mmol), HOBt (0.044 g, 0.33 mmol), and EDCI (0.062 g, 0.33 mmol), in DMF (10 mL), was added N-methyl morpholine (0.034 g, 0.33 mmom). The resulting mixture was stirred at room temperature overnight followed by dilution with DCM. The reaction mixture was poured into water; organic layer was washed with water, brine, dried over sodium sulfate, and the organic solvent evaporated to get a residue which was purified by column chromatoghaphy using 40-50% ethylacetate in hexane as eluent to provide the title compound (0.045 g).

Workup

  1. washorganic layer was washed with water, brine
  2. dry with materialdried over sodium sulfate
  3. customthe organic solvent evaporated
  4. customto get a residue which
  5. customwas purified by column chromatoghaphy

Sources & evidence

ORD record
ord-5c6e757e906644d6bc995ef116271db8
Source dataset
uspto-grants-2013_08
Patent number
US08501955B2

Reaction notes

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