Triethyloxonium tetrafluoroborate → HCID 66599238, compound

HRID 1889105Notes

Reaction equation

HRID 1889105 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[C:6]([Cl:9])[CH:5]=[CH:4][C:3]=1[C:10]([N:12]1[CH2:17][CH2:16][NH:15][C:14](=O)[CH2:13]1)=[O:11].F[B-](F)(F)F.C([O+](CC)CC)C.[CH3:31][C:32]1[S:36][C:35]([C:37]([NH:39][NH2:40])=O)=[N:34][CH:33]=1>ClCCl>[Cl:1][C:2]1[C:7]([F:8])=[C:6]([Cl:9])[CH:5]=[CH:4][C:3]=1[C:10]([N:12]1[CH2:17][CH2:16][N:15]2[C:37]([C:35]3[S:36][C:32]([CH3:31])=[CH:33][N:34]=3)=[N:39][N:40]=[C:14]2[CH2:13]1)=[O:11]

Participants

5

Reactant 3

HCID 2723982Triethyloxonium tetrafluoroborateHCID 451227225-Methyl-1,3-thiazole-2-carbohydrazideHCID 665993614-[(2,4-Dichloro-3-fluorophenyl)carbonyl]-2-piperazinone

Product 1

HCID 66599238HCID 66599238, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
110 °C

Procedure

A solution of 4-[(2,4-dichloro-3-fluorophenyl)carbonyl]-2-piperazinone (I37) (329 mg, 1.13 mmol) in dry dichloromethane (DCM) (1413 μl) was stirred at room temperature under an atmosphere of argon. Triethyloxonium tetrafluoroborate (236 mg, 1.243 mmol) was added and the mixture was stirred for 1 hour. After this time, 5-methyl-1,3-thiazole-2-carbohydrazide (I117) (224 mg, 1.425 mmol) was added and the mixture was stirred for a further 60 hours (over weekend). The solvent was removed under reduced pressure. The resulting residue was dissolved in 1-butanol (1413 μl) and the solution was heated to 110° C. for 4 hours. The solution was concentrated under reduced pressure and the residue dissolved in DCM (approx. 40 ml). The organics were washed with NaHCO3 (sat. aqueous solution approx. 20 ml), before being dried over MgSO4, filtered and concentrated under reduced pressure to give a yellow coloured oil. The oil was chromatographed [SiO2, 0-10% MeOH in DCM] then further purified using MDAP (formic acid method) to give a white coloured solid of desired product in 74 mg.

Workup

  1. stirringthe mixture was stirred for a further 60 hours (over weekend)
  2. customThe solvent was removed under reduced pressure
  3. dissolutionThe resulting residue was dissolved in 1-butanol (1413 μl)
  4. concentrationThe solution was concentrated under reduced pressure
  5. dissolutionthe residue dissolved in DCM (approx. 40 ml)
  6. washThe organics were washed with NaHCO3 (sat. aqueous solution approx. 20 ml)
  7. dry with materialbefore being dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customto give a yellow coloured oil
  11. customThe oil was chromatographed [SiO2, 0-10% MeOH in DCM]
  12. customthen further purified

Sources & evidence

ORD record
ord-0a408e1609c44147ae89f047b395586c
Source dataset
uspto-grants-2013_08
Patent number
US08501946B2

Reaction notes

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