Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Methyl 6-aminohexanoate hydrochloride | HCID 11499324 | — |
| Reactant | 8-(Cyclohexylmethoxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylic acid | HCID 71108490 | — |
| Reactant | HCID 178484679 | HCID 178484679 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | HCID 86718238 | HCID 86718238 | — |
Reaction Steps
18 mg of methyl 6-aminohexanoate hydrochloride (0.1 mmol, 1.0 equivalent) were initially charged, and 29 mg of 8-(cyclohexylmethoxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylic acid Example 6A (0.1 mmol, 1 equivalent) in 0.3 ml of DMSO, 41.7 mg of (benzotriazol-1-yloxy)bisdimethylaminomethyliumfluoroborate (TBTU, 0.13 mmol, 1.3 equivalents) in 0.3 ml of DMSO and 26 mg of N,N-diisopropylethylamine (0.2 mmol, 2 equivalents) were added in succession. The mixture was shaken at RT overnight, 0.4 ml of 2 N sodium hydroxide solution was added and the mixture was once more shaken at RT overnight. The solvent was then evaporated and the mixture was purified by preparative HPLC (Method 10). This gave 11 mg (26% of theory; purity: 100%) of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08796305B2 |
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| Source dataset | uspto-grants-2014_08 |
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| ORD ID | ord-7cf2d8cdd5a34822946ee35b8b475e11 |
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| Source note | uspto-grants-2014_08 |
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