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

HRID 524421Notes

Reaction equation

HRID 524421 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.C(Cl)(=O)C(Cl)=O.[NH2:30][C:31]1[S:32][CH:33]=[CH:34][N:35]=1.Cl>C(Cl)Cl.N1C=CC=CC=1.CN(C=O)C>[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:30][C:31]3[S:32][CH:33]=[CH:34][N:35]=3)=[O:15])=[CH:11][CH:12]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 21552-AminothiazoleHCID 65578Oxalyl chlorideHCID 59610020(4-Cyclopropanesulfonyl-phenyl)-[(tetrahydro-pyran-4-yloxy)]-acetic acid

Product 1

HCID 888617632-(4-Cyclopropylsulfonylphenyl)-2-tetrahydropyran-4-yloxy-N-thiazol-2-yl-acetamide

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

2-(4-Cyclopropylsulfonylphenyl)-2-tetrahydropyran-4-yloxy-acetic acid (preparation 4) was dissolved in DCM. To this solution was added DMF and cooled to 0° C., followed by the addition of oxalyl chloride under stirring. To this mixture, a solution of 2-aminothiazole and pyridine in DCM was added drop wise at 0° C. and was stirred further for 4 h. at room temperature. The reaction mixture was poured into IN aqueous HCl under stirring, organic layer was again washed with 1N HCl, followed by 5% brine, dried over anhydrous sodium sulfate, solvent was removed under reduced pressure to get the crude compound which was purified by flash chromatography to get the title product.

Workup

  1. stirringwas stirred further for 4 h. at room temperature
  2. stirringunder stirring
  3. washorganic layer was again washed with 1N HCl
  4. dry with materialdried over anhydrous sodium sulfate, solvent
  5. customwas removed under reduced pressure
  6. customto get the crude compound which
  7. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-9ff630c38c4345018f775ab7b966c184
Source dataset
uspto-grants-2016_05
Patent number
US09340506B2

Reaction notes

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