Hydrochloric Acid → HCID 4873430, compound

HRID 2196518Notes

Reaction equation

HRID 2196518 reaction equation
[NH:1]([C:3]1[S:4][CH:5]=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:7]=1)[NH2:2].Cl.O1CCOCC1.[F:20][C:21]([F:33])([F:32])[C:22](=O)[CH2:23][C:24]([C:26]1[O:27][CH:28]=[CH:29][CH:30]=1)=O>C(O)C>[O:27]1[CH:28]=[CH:29][CH:30]=[C:26]1[C:24]1[N:1]([C:3]2[S:4][CH:5]=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:7]=2)[N:2]=[C:22]([C:21]([F:20])([F:32])[F:33])[CH:23]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 675944,4,4-Trifluoro-1-(2-furanyl)-1,3-butanedioneHCID 14181283Ethyl 2-hydrazinyl-1,3-thiazole-4-carboxylate

Product 1

HCID 4873430HCID 4873430, compoundYield 39.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

To 28 (268 mg, 1.431 mmol) was added 4N HCl in dioxane (3.6 mL, 14.3 mmol) and 4,4,4-trifluoro-1-(2-furyl)-1,3-butanedione (0.23 mL, 1.6 mmol). The resulting suspension was allowed to stir for 16 h at 100° C. Ethanol (1.4 mL) was added, and the mixture was stirred for 4 h at 100° C. Solvent was evaporated and the residue was purified by silica gel column chromatography with gradient of EtOAc (10-20%) in hexanes to afford 29 (203 mg, 20%) as an orange solid. LRMS (ESI): calc. 357.0; found 358.1 (MH)+.

Workup

  1. stirringthe mixture was stirred for 4 h at 100° C
  2. customSolvent was evaporated
  3. customthe residue was purified by silica gel column chromatography with gradient of EtOAc (10-20%) in hexanes

Sources & evidence

ORD record
ord-6a21facb4c9c4b97a007af5526ce2b86
Source dataset
uspto-grants-2012_12
Patent number
US08338437B2

Reaction notes

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