2-Aminothiazole → 3-Cyclopentyl-2-(4-methanesulfonyl-phenyl)-N-thiazol-2-yl-propionamide

HRID 1159466Notes

Reaction equation

HRID 1159466 reaction equation
[CH:1]1([CH2:6][CH:7]([C:11]2[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][CH:12]=2)[C:8]([OH:10])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.CN(C=O)C.[NH2:26][C:27]1[S:28][CH:29]=[CH:30][N:31]=1>S(Cl)(Cl)=O.C(Cl)Cl.N1C=CC=CC=1>[CH:1]1([CH2:6][CH:7]([C:11]2[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][CH:12]=2)[C:8]([NH:26][C:27]2[S:28][CH:29]=[CH:30][N:31]=2)=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

7

Reactant 3

HCID 21552-AminothiazoleHCID 6228DimethylformamideHCID 120694893-Cyclopentyl-2-(4-methanesulfonyl-phenyl)propionic acid

Product 1

HCID 97999423-Cyclopentyl-2-(4-methanesulfonyl-phenyl)-N-thiazol-2-yl-propionamide

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6344DichloromethaneSolventHCID 24386Thionyl ChlorideSolvent

Procedure

The title B compound, 3-cyclopentyl-2-(4-methanesulfonyl-phenyl)-propionic acid (3.44 mmol, 1.02 g) is suspended in thionyl chloride (5 mL) with a catalytic amount of DMF and stirred for 12 h. The mixture is evaporated and then diluted with toluene and re-evaporated to afford an oil which is diluted with 4 mL of DCM and added to 2-aminothiazole (3.8 mmol, 0.4 g) in 10 mL of pyridine at 0° C. and then stirred for 12 h while warming to RT. The reaction mixture is evaporated, diluted with EtOAc and 0.1 N HCl and the organic solution is washed with brine, dried and evaporated to an oil. Chromatography on silica (eluent: 5%→25% EtOAc in hexanes) affords 3-cyclopentyl-2-(4-methanesulfonyl-phenyl)-N-thiazol-2-yl-propionamide: 1H NMR δ 11.7 (s, 1H), 7.86 (d, J=8, 2H), 7.55 (d, J=3.5, 1H), 7.53 (d, J=8, 2H), 7.10 (d, J=3.5, 1H), 3.81 (t, J=7.5, 1H), 3.03 (s, 3H), 1.1-2.2 (m, 11H).

Workup

  1. customThe mixture is evaporated
  2. additiondiluted with toluene
  3. customre-evaporated
  4. customto afford an oil which
  5. stirringstirred for 12 h
  6. customThe reaction mixture is evaporated
  7. additiondiluted with EtOAc and 0.1 N HCl
  8. washthe organic solution is washed with brine
  9. customdried
  10. customevaporated to an oil

Sources & evidence

ORD record
ord-64ec6f6b52084cbeb26c8626021c5959
Source dataset
uspto-grants-2010_10
Patent number
US07812167B2

Reaction notes

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