Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Isobutyric Acid | HCID 6590 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | 1-Hydroxybenzotriazole hydrate | HCID 2796029 | — |
| Reactant | HCID 68873899 | HCID 68873899 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 57721186 | HCID 57721186 | 31% |
Reaction Steps
A solution of the product of Step 4 (80 mg, 0.20 mmol) and 2-methylpropanoic acid (18.4 mg, 0.21 mmol) in 2 ml DMF was treated with 1-hydroxybenzotriazole hydrate (HOBT)(29.7 mg, 0.22 mmol). The resulting mixture was stirred for 10 minutes at room temperature before being treated with triethylamine (22 mg, 0.22 mmol) and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (EDC) (42 mg, 0.22 mmol). The reaction was kept at room temperature overnight. Purification of the crude mixture by reverse phase (CH3CN 30%-80% in H2O with 0.1% TFA) afforded 20 mg (31%) oil as title compound. 1H NMR (400 MHz, DMSO-D6) δ ppm 8.89 (s, 1H), 7.68 (d, 2H, 8.8 Hz), 7.38 (d, 2H, 8.8 Hz), 7.32 (t, 1H, 8.0 Hz), 6.85 (d, 1H, 7.6 Hz), 6.79-6.91 (m, 3H), 5.5-6.8 (M, 6H), 2.88 (m, 1H), 1.28 (d, 6H, 6.8 Hz). MS (ES+) m/e 372.2 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07547779B2 |
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| Source dataset | uspto-grants-2009_06 |
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| ORD ID | ord-c4ea1d5a09c94bd6897e3d802c58d7a2 |
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| Source note | uspto-grants-2009_06 |
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