Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Glycolic Acid | HCID 757 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | HCID 67265437 | HCID 67265437 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 67265520 | HCID 67265520 | — |
Reaction Steps
To a solution of glycolic acid (15 mg, 202 μmol) and DIPEA (35 mg, 270 μmol) in DMF (5 mL) is added HOBt (27 mg, 202 μmol) and EDC hydrochloride (39 mg, 202 μmol) at 0° C. The mixture is stirred for 15 min at 0° C. Then 2-{4-[5-(5-diethylaminomethyl-4-methyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-ethylamine is added and stirring is continued for 1 h at 0° C. The reaction is quenched with water, diluted with sat. aq. NaHCO3 and the mixture is extracted three times with EA. The combined organic extracts are dried over MgSO4, filtered and concentrated. The crude product is purified on prep. TLC plates using DCM containing 10% of 7 N NH3 in methanol to give the title compound (4 mg) as a colourless oil; LC-MS: tR=0.69 min; [M+1]+=429.06.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08148410B2 |
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| Source dataset | uspto-grants-2012_04 |
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| ORD ID | ord-e733ef2d545a41968c2e145ece6a88eb |
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| Source note | uspto-grants-2012_04 |
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