2-Aminothiazole → HCID 9800577, compound

HRID 1350307Notes

Reaction equation

HRID 1350307 reaction equation
N=C=N.[CH3:4][S:5]([C:8]1[CH:13]=[CH:12][C:11](/[C:14](=[CH:18]\[C:19]2[CH:23]=[CH:22][S:21][CH:20]=2)/[C:15]([OH:17])=O)=[CH:10][CH:9]=1)(=[O:7])=[O:6].C1C=CC2N(O)N=NC=2C=1.[S:34]1[CH:38]=[CH:37][N:36]=[C:35]1[NH2:39]>CN(C=O)C>[CH3:4][S:5]([C:8]1[CH:9]=[CH:10][C:11](/[C:14](=[CH:18]\[C:19]2[CH:23]=[CH:22][S:21][CH:20]=2)/[C:15]([NH:39][C:35]2[S:34][CH:38]=[CH:37][N:36]=2)=[O:17])=[CH:12][CH:13]=1)(=[O:6])=[O:7]

Participants

6

Reactant 4

HCID 21552-AminothiazoleHCID 757711-HydroxybenzotriazoleHCID 160435CarbodiimideHCID 58860794HCID 58860794, compound

Product 1

HCID 9800577HCID 9800577, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

A suspension of PS-carbodiimide (688 mg, loading 1.34 μmol mg−1, 922 μmol), (E)-2-(4-methanesulfonylphenyl)-3-thiophen-3-ylacrylic acid (Preparation 1, 139 mg, 450 μmol), and HOBt (84 mg, 622 μmol) in anhydrous DMF was stirred for 15 min at 20° C. Thiazol-2-ylamine (32 mg, 320 μmol) was added, then the mixture was stirred for 40 h at 20° C., before being filtered through Celite. The filter cake was washed with DMF (10 mL), EtOAc (20 mL), and CH2Cl2 (20 mL). The solutions were combined, the solvents removed under reduced pressure, and the residue dissolved in EtOAc (50 mL). The EtOAc solution was washed with saturated aqueous Na2CO3 (3×20 mL), H2O (20 mL), and brine (20 mL), before being dried (Na2SO4). Filtration, solvent evaporation, and flash chromatography (IH-EtOAc, 3:1 to 1:3) gave the title compound: RTA=3.43 min; m/z (ES+)=391.0 [M+H]+.

Workup

  1. stirringthe mixture was stirred for 40 h at 20° C.
  2. filtrationbefore being filtered through Celite
  3. washThe filter cake was washed with DMF (10 mL), EtOAc (20 mL), and CH2Cl2 (20 mL)
  4. customthe solvents removed under reduced pressure
  5. dissolutionthe residue dissolved in EtOAc (50 mL)
  6. washThe EtOAc solution was washed with saturated aqueous Na2CO3 (3×20 mL), H2O (20 mL), and brine (20 mL)
  7. dry with materialbefore being dried (Na2SO4)
  8. filtrationFiltration, solvent evaporation, and flash chromatography (IH-EtOAc, 3:1 to 1:3)

Sources & evidence

ORD record
ord-a20f7b039db54f1c9488ae0de715c5db
Source dataset
uspto-grants-2007_05
Patent number
US07214681B2

Reaction notes

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