2-Aminothiazole → HCID 10020462, compound

HRID 855544Notes

Reaction equation

HRID 855544 reaction equation
[CH:1]1(/[CH:6]=[C:7](\[C:11]2[CH:16]=[CH:15][C:14]([S:17][CH3:18])=[CH:13][N:12]=2)/[C:8]([OH:10])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[S:40]1[CH:44]=[CH:43][N:42]=[C:41]1[NH2:45]>C1COCC1.CN(C=O)C>[CH:1]1(/[CH:6]=[C:7](\[C:11]2[CH:16]=[CH:15][C:14]([S:17][CH3:18])=[CH:13][N:12]=2)/[C:8]([NH:45][C:41]2[S:40][CH:44]=[CH:43][N:42]=2)=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

7

Reactant 4

HCID 21552-AminothiazoleHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 58935718HCID 58935718, compound

Product 1

HCID 10020462HCID 10020462, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (E)-3-cyclopentyl-2-(5-methylsulfanylpyridin-2-yl)acrylic acid (Preparation 5, 1.00 g, 3.8 mmol), EDCI (0.95 g, 4.9 mmol), HOBt (0.67 g, 4.9 mmol) and thiazol-2-ylamine (1.52 g, 15.2 mmol) in anhydrous THF (62 mL) and DMF (50 mL) was stirred at 20° C. for 4 d. The solvents were evaporated off under reduced pressure, then the residue was partitioned between CH2Cl2 and saturated aqueous Na2CO3. The organic layer was washed with H2O and brine, before being dried (MgSO4). Filtration, solvent evaporation, and column chromatography (7:31H-EtOAc) provided the title compound: RTA=3.96 min; m/z (ES+)=346.1 [M+H]+.

Workup

  1. customThe solvents were evaporated off under reduced pressure
  2. customthe residue was partitioned between CH2Cl2 and saturated aqueous Na2CO3
  3. washThe organic layer was washed with H2O and brine
  4. dry with materialbefore being dried (MgSO4)
  5. filtrationFiltration, solvent evaporation, and column chromatography (7:31H-EtOAc)

Sources & evidence

ORD record
ord-f14d41ec58744a0f8120c2849a86108f
Source dataset
uspto-grants-2007_08
Patent number
US07262196B2

Reaction notes

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