1-Butanol → HCID 66598916, compound

HRID 1889099Notes

Reaction equation

HRID 1889099 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.[S:31]1[C:35]([C:36]([NH:38][NH2:39])=O)=[CH:34][CH:33]=[N:32]1.C(O)CCC>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:36]([C:35]3[S:31][N:32]=[CH:33][CH:34]=3)=[N:38][N:39]=[C:14]2[CH2:13]1)=[O:11]

Participants

6

Reactant 4

HCID 2631-ButanolHCID 2723982Triethyloxonium tetrafluoroborateHCID 552818681,2-Thiazole-5-carbohydrazideHCID 665993614-[(2,4-Dichloro-3-fluorophenyl)carbonyl]-2-piperazinone

Product 1

HCID 66598916HCID 66598916, 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)(244 mg, 0.839 mmol) in dry dichloromethane (DCM) (2098 μl) was stirred at room temperature under an atmosphere of argon. Triethyloxonium tetrafluoroborate (175 mg, 0.923 mmol) was added and the resulting mixture was stirred for ¾ hours. After this time, 5-isothiazolecarbohydrazide (I84) (153 mg, 1.069 mmol) was added and the resulting mixture was stirred at room temperature for 60 hours (over the weekend). 1-Butanol (2098 μl) was added and the reaction mixture was heated to 110° C. for 2 hours. The solution was allowed to cool to room temperature and the solvent was removed under reduced pressure. The residue was partitioned between DCM (approx 40 ml) and NaHCO3 (saturated aqueous solution approx. 20 ml). The organic phases were dried over MgSO4, filtered and concentrated under reduced pressure to give a pale yellow coloured solid. The solid was purified using MDAP to give a white coloured solid.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 60 hours (over the weekend)
  2. temperatureto cool to room temperature
  3. customthe solvent was removed under reduced pressure
  4. customThe residue was partitioned between DCM (approx 40 ml) and NaHCO3 (saturated aqueous solution approx. 20 ml)
  5. dry with materialThe organic phases were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give a pale yellow coloured solid
  9. customThe solid was purified
  10. customto give a white coloured solid

Sources & evidence

ORD record
ord-2dc4fbf7431f4464bc389a700aa0bc0b
Source dataset
uspto-grants-2013_08
Patent number
US08501946B2

Reaction notes

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