Dimethylformamide → HCID 68782162, compound

HRID 2263073Notes

Reaction equation

HRID 2263073 reaction equation
FC(F)(F)C(O)=O.[CH3:8][C:9]1[C:13]([CH3:14])=[C:12]([NH:15][C:16]([N:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)=[O:17])[O:11][N:10]=1.Cl[C:25]1[S:29][N:28]=[C:27]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[F:36])[N:26]=1.C(N(CC)CC)C.CN(C)C=O>O>[CH3:8][C:9]1[C:13]([CH3:14])=[C:12]([NH:15][C:16]([N:18]2[CH2:19][CH2:20][N:21]([C:25]3[S:29][N:28]=[C:27]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=4[F:36])[N:26]=3)[CH2:22][CH2:23]2)=[O:17])[O:11][N:10]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 463184775-Chloro-3-(2-fluorophenyl)-1,2,4-thiadiazoleHCID 68778028HCID 68778028, compound

Product 1

HCID 68782162HCID 68782162, compoundYield 15.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of N-(3,4-dimethylisoxazol-5-yl)piperazine-1-carboxamide trifluoroacetate (297 mg, 0.707 mmol), 5-chloro-3-(2-fluorophenyl)-1,2,4-thiadiazole (152 mg, 0.707 mmol), triethylamine (0.491 ml, 3.53 mmol) and N,N-dimethylformamide (3 ml) was stirred at room temperature for 0.5 hours, the reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was recrystallized from a mixed solvent of tetrahydrofuran and ethyl acetate to obtain the desired product (44.0 mg, 15.5%) as a solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was recrystallized from a mixed solvent of tetrahydrofuran and ethyl acetate

Sources & evidence

ORD record
ord-f08a208afd134c3ab6604e05e104017b
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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