Water → HCID 19608315, compound

HRID 1602857Notes

Reaction equation

HRID 1602857 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=1)[C:6](Cl)=[O:7].C(N(CC)CC)C.[CH3:25][C:26]1[N:30]=[C:29]([C:31]2[N:32]=[N:33][C:34]([N:37]3[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]3)=[CH:35][CH:36]=2)[S:28][N:27]=1.O>C(Cl)Cl>[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=1)[C:6]([N:40]1[CH2:39][CH2:38][N:37]([C:34]2[N:33]=[N:32][C:31]([C:29]3[S:28][N:27]=[C:26]([CH3:25])[N:30]=3)=[CH:36][CH:35]=2)[CH2:42][CH2:41]1)=[O:7]

Participants

6

Reactant 4

HCID 962WaterHCID 8471Triethylamine2×HCID 1018563,5-Bis(trifluoromethyl)benzoyl chlorideHCID 19608320HCID 19608320, compound

Product 1

HCID 19608315HCID 19608315, compoundYield 45.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3,5-bis(trifluoromethyl)-benzoyl chloride (1.1 g) and triethylamine (0.4 g) in DCM (40 ml) was stirred. 3-(3-methyl-1,2,4-thiadiazol-5-yl)-6-(1-piperazinyl)-pyridazine (1.1 g) was added portionwise. The mixture was stirred at room temperature for 3 hours. Triethylamine was added. The mixture was stirred at room temperature for 1 hour. Water was added and the mixture was extracted three times with DCM. The combined organic layer was dried, filtered and the solvent was evaporated. The residue was crystallized from methanol. The precipitate was filtered off and dried, yielding 0.91 g (45%) of 1-[3,5-bis(trifluoromethyl)benzoyl]-4-[6-(3-methyl-1,2,4-thiadiazol-5-yl)-3-pyridazinyl]piperazine (compound 131).

Workup

  1. stirringThe mixture was stirred at room temperature for 3 hours
  2. stirringThe mixture was stirred at room temperature for 1 hour
  3. extractionthe mixture was extracted three times with DCM
  4. customThe combined organic layer was dried
  5. filtrationfiltered
  6. customthe solvent was evaporated
  7. customThe residue was crystallized from methanol
  8. filtrationThe precipitate was filtered off
  9. customdried

Sources & evidence

ORD record
ord-2005d7d0eb2e48f386f59f6c36435c1e
Source dataset
uspto-grants-1999_11
Patent number
US05985878

Reaction notes

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