1,2,3-Thiadiazole-4-carboxylic acid, hydrazide → HCID 66599284, compound

HRID 1889106Notes

Reaction equation

HRID 1889106 reaction equation
F[B-](F)(F)F.C([O+](CC)CC)C.[Cl:13][C:14]1[C:19]([F:20])=[C:18]([Cl:21])[CH:17]=[CH:16][C:15]=1[C:22]([N:24]1[CH2:29][CH2:28][NH:27][C:26](=O)[CH2:25]1)=[O:23].[S:31]1[CH:35]=[C:34]([C:36]([NH:38][NH2:39])=O)[N:33]=[N:32]1>ClCCl>[Cl:13][C:14]1[C:19]([F:20])=[C:18]([Cl:21])[CH:17]=[CH:16][C:15]=1[C:22]([N:24]1[CH2:29][CH2:28][N:27]2[C:36]([C:34]3[N:33]=[N:32][S:31][CH:35]=3)=[N:38][N:39]=[C:26]2[CH2:25]1)=[O:23]

Participants

5

Reactant 3

HCID 727201,2,3-Thiadiazole-4-carboxylic acid, hydrazideHCID 2723982Triethyloxonium tetrafluoroborateHCID 665993614-[(2,4-Dichloro-3-fluorophenyl)carbonyl]-2-piperazinone

Product 1

HCID 66599284HCID 66599284, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethyloxonium tetrafluoroborate (363 mg, 1.908 mmol) was added to a suspension of 4-[(2,4-dichloro-3-fluorophenyl)carbonyl]-2-piperazinone (I37)(505 mg, 1.735 mmol) in dry dichloromethane (DCM) (4.2 ml). The reaction mixture was stirred at room temperature 45 mins—until everything was dissolved. 1,2,3-Thiadiazole-4-carbohydrazide (300 mg, 2.082 mmol, commercially available from e.g. Apollo) was added and the resulting mixture was stirred at room temperature for 3 h. DCM was evaporated and the residue was dissolved into 1-butanol (4.2 ml). The reaction mixture was stirred at reflux for 19 h. The mixture was washed with ethyl acetate and washed with water (2×25 mL) and brine (2×25 mL). The resulting organic layer was dried over MgSO4 and dried under reduced pressure. The crude product was purified by flash chromatography (DCM−10% MeOH in DCM). The residue was triturated with Et2O and then dried under vacuum at 50° C. for 2 days. The resulting solid was triturated with n-hexane and dried at 50° C. under vacuum 20 h to afford the desired product in 4.71 mg, as a white solid.

Workup

  1. dissolutionwas dissolved
  2. stirringthe resulting mixture was stirred at room temperature for 3 h
  3. customDCM was evaporated
  4. dissolutionthe residue was dissolved into 1-butanol (4.2 ml)
  5. stirringThe reaction mixture was stirred
  6. temperatureat reflux for 19 h
  7. washThe mixture was washed with ethyl acetate
  8. washwashed with water (2×25 mL) and brine (2×25 mL)
  9. dry with materialThe resulting organic layer was dried over MgSO4
  10. customdried under reduced pressure
  11. customThe crude product was purified by flash chromatography (DCM−10% MeOH in DCM)
  12. customThe residue was triturated with Et2O
  13. customdried under vacuum at 50° C. for 2 days
  14. customThe resulting solid was triturated with n-hexane
  15. customdried at 50° C. under vacuum 20 h

Sources & evidence

ORD record
ord-6838d906bbd0412bb1a8fdc4828ce91e
Source dataset
uspto-grants-2013_08
Patent number
US08501946B2

Reaction notes

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