Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 3-Chlorophenylacetic acid | HCID 15879 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | 2-(4-Nitrophenyl)-1-(2-thiophene-2-ylthiazol-4-yl)ethylamine | HCID 66705334 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 59464692 | HCID 59464692 | 60% |
Reaction Steps
To a solution of 2-(4-nitropheyl)-1-(2-thiophene2-ylthiazol-4-yl)ethylamine, 22,(0.41 g, 1 mmol) 3-chlorophenylacetic acid (0.170 g, 1mmol) and 1-hydroxybenzotriazole (HOBt)(0.07 g, 0.05 mmol) in DMF (5 ml) at 0°, is added 1-(3-dimethylaminoprpyl)-3-ethylcarbodiimide (EDCI) (0.190 g, 1 mmol) followed by triethylamine (0.42 mL, 3 mmol). The mixture is stirred at 0° for 30 minutes then at room temperature overnight. The reaction mixture is diluted with water and extracted with EtOAc. The combined organic phase is washed with 1 N aqueous HCI, 5% aqueoue NaHCO3, water and brine, and dried over Na2SO4. The solvent is removed in vacuo to afford 0.290 g (60% yield) of the desired product wich is used without further purification. SEI-MS 428 (M-1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08569348B2 |
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| Source dataset | uspto-grants-2013_10 |
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| ORD ID | ord-0473cb49042e4a1a85d8432869044ba5 |
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| Source note | uspto-grants-2013_10 |
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