Diisopropylethylamine → HCID 68779982, compound

HRID 2263178Notes

Reaction equation

HRID 2263178 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8](=[O:15])OCC(Cl)(Cl)Cl)[CH:2]=1.[F:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23]1[N:24]=[C:25]([N:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)[S:26][CH:27]=1.C(N(C(C)C)CC)(C)C>O>[F:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23]1[N:24]=[C:25]([N:28]2[CH2:29][CH2:30][N:31]([C:8]([NH:7][C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)=[O:15])[CH2:32][CH2:33]2)[S:26][CH:27]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 581827331-[4-(2-Fluorophenyl)-1,3-thiazol-2-yl]piperazineHCID 685753802,2,2-Trichloroethyl pyridin-3-ylcarbamate

Product 1

HCID 68779982HCID 68779982, compoundYield 31.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2,2,2-trichloroethyl pyridin-3-ylcarbamate (225 mg, 0.835 mmol), 1-[4-(2-fluorophenyl)-1,3-thiazol-2-yl]piperazine (200 mg, 0.760 mmol) and diisopropylethylamine (0.265 ml, 1.52 mmol) in dimethylsufoxide (2.5 ml) was stirred at 70° C. for 12 hours. Water was poured into the reaction solution, and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulafate, and the solvent was distilled off under reduced pressure. The residue was recrystallized from a mixed solvent of hexane and ethyl acetate to give the desired product (90.9 mg, 31.2%) 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 sulafate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was recrystallized from a mixed solvent of hexane and ethyl acetate

Sources & evidence

ORD record
ord-8db35b5fe40f420a801346358cdbcfb6
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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