2-Aminothiazole → 2-(4-Cyclopropanesulfonylphenyl)-2-(2,4-difluoro-phenoxy)-N-thiazol-2-yl-acetamide

HRID 1889190Notes

Reaction equation

HRID 1889190 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.[NH2:26][C:27]1[S:28][CH:29]=[CH:30][N:31]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>C(Cl)Cl.O.C(N(CC)CC)C>[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:26][C:27]3[S:28][CH:29]=[CH:30][N:31]=3)=[O:15])=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:2][CH2:3]1

Participants

8

Reactant 4

HCID 21552-AminothiazoleHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 596100322-(4-Cyclopropylsulfonylphenyl)-2-(2,4-difluorophenoxy)acetic acid

Product 1

HCID 252619862-(4-Cyclopropanesulfonylphenyl)-2-(2,4-difluoro-phenoxy)-N-thiazol-2-yl-acetamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

Procedure-A: To a mixture of 2-(4-cyclopropanesulfonylphenyl)-2-(2,4-difluorophenoxy)acetic acid (obtained in step III), 2-aminothiazole, HOBt, and EDCI, in methylene chloride, was added triethyl amine. The resulting mixture was stirred at room temperature overnight followed by dilution with methylene chloride. 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 preparative TLC or column chromatoghaphy to provide the title compound.

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 preparative TLC or column chromatoghaphy

Sources & evidence

ORD record
ord-959577735b364c9ba5b181a161f104ca
Source dataset
uspto-grants-2013_08
Patent number
US08501955B2

Reaction notes

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