Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | Thian-4-amine--hydrogen chloride (1/1) | HCID 18331311 | — |
| Reactant | 2-[4-(2-Tert-butylphenyl)piperazin-1-yl]-2-oxoacetic acid | HCID 66750854 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 66792717 | HCID 66792717 | 82% |
Reaction Steps
A mixture of 2-[4-(2-tert-butylphenyl)piperazin-1-yl]-2-oxoacetic acid (Example 44, 0.60 g, 2.07 mmol), tetrahydro-2H-thiopyran-4-amine hydrochloride (0.23 g, 2.48 mmol), triethylamine (433 μL, 3.11 mmol), EDCI (0.39 g, 2.48 mmol) and HOBt (0.38 g, 2.48 mmol) in N,N-dimethylformamide (10 mL) was stirred at room temperature for 4 days. The reaction mixture was poured into saturated NaHCO3 solution and extracted with ethyl acetate. The extract was washed with saturated NaHCO3 solution and brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate 90:10 to 50:50) to give the title compound (0.23 g, 82%) as a white amorphous.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08853215B2 |
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| Source dataset | uspto-grants-2014_10 |
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| ORD ID | ord-cd40733f85784a2d8d4397da942e0011 |
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| Source note | uspto-grants-2014_10 |
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