Dimethyl Sulfoxide → HCID 68782018, compound

HRID 2263118Notes

Reaction equation

HRID 2263118 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([NH:13][C:14](=[O:21])OCC(Cl)(Cl)Cl)=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[C:22]1([C:28]2[N:29]=[C:30]([N:33]3[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]3)[S:31][CH:32]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(N(C(C)C)CC)(C)C.CS(C)=O>O>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([NH:13][C:14]([N:36]3[CH2:37][CH2:38][N:33]([C:30]4[S:31][CH:32]=[C:28]([C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)[N:29]=4)[CH2:34][CH2:35]3)=[O:21])=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 7124681-(4-Phenyl-1,3-thiazol-2-yl)piperazineHCID 86625498HCID 86625498, compound

Product 1

HCID 68782018HCID 68782018, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2,2,2-trichloroethyl (1-acetyl-2,3-dihydro-1H-indol-5-yl)carbamate (200 mg, 0.569 mmol), 1-(4-phenyl-1,3-thiazol-2-yl)piperazine (140 mg, 0.569 mmol), diisopropylethylamine (0.198 ml, 1.14 mmol) and dimethylsulfoxide (4 ml) was stirred at 70° C. for 48 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. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate) to obtain the desired product. This was recrystallized from a mixed solvent of tetrahydrofuran, ethyl acetate and hexane to obtain the desired product (92.0 mg, 36.1%) 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 purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-7ac3d551e64244cbab1a0ade8dd16a77
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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