2-Aminothiazole → 2-(4-Cyclopropylsulfonylphenyl)-2-tetrahydropyran-4-yloxy-N-thiazol-2-yl-acetamide

HRID 524420Notes

Reaction equation

HRID 524420 reaction equation
[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([O:17][CH:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[C:14](O)=[O:15])=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.[NH2:24][C:25]1[S:26][CH:27]=[CH:28][N:29]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.CN1CCOCC1>C(Cl)Cl.O>[CH:1]1([S:4]([C:7]2[CH:8]=[CH:9][C:10]([CH:13]([O:17][CH:18]3[CH2:19][CH2:20][O:21][CH2:22][CH2:23]3)[C:14]([NH:24][C:25]3[S:26][CH:27]=[CH:28][N:29]=3)=[O:15])=[CH:11][CH:12]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1

Participants

8

Reactant 5

HCID 21552-AminothiazoleHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59610020(4-Cyclopropanesulfonyl-phenyl)-[(tetrahydro-pyran-4-yloxy)]-acetic acid

Product 1

HCID 888617632-(4-Cyclopropylsulfonylphenyl)-2-tetrahydropyran-4-yloxy-N-thiazol-2-yl-acetamideYield 48.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 2-(4-cyclopropylsulfonylphenyl)-2-tetrahydropyran-4-yloxy-acetic acid (preparation 4; 0.2 g, 0.58 mmol), 2-aminothiazole (0.070 g, 0.70 mmol), HOBt (0.095 g), and EDCl (0.134 g, 0.70 mmol) in methylene chloride (6 mL), was added N-methyl morpholine (0.08 mL, 0.70 mmol). 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 to obtain a title compound (0.118 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 preparative TLC

Sources & evidence

ORD record
ord-1e5bce55eb0543f4a1162636caa28399
Source dataset
uspto-grants-2016_05
Patent number
US09340506B2

Reaction notes

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