Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | ethyl (1R,2S)-2-aminocyclohexane-1-carboxylate hydrochloride | HCID 2724641 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | HCID 78321671 | HCID 78321671 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 78321672 | HCID 78321672 | — |
Reaction Steps
A mixture of (R)-1-(4′-(2-(2-methylpyrrolidin-1-yl)ethyl)biphenyl-4-yl)cyclopentanecarboxylic acid (15 mg, 0.040 mmol), (1R,2S)-ethyl 2-aminocyclohexanecarboxylate hydrochloride (9.08 mg, 0.044 mmol), HATU (16.62 mg, 0.044 mmol), and TEA (0.017 mL, 0.119 mmol) in DMF (0.4 mL) was stirred at room temperature overnight. The mixture was acidified with 1M HCl and purified by HPLC to give the title compound. LCMS m/z=531.7 [M+H]+; 1H NMR (400 MHz, CD3CN) δ ppm 1.13 (t, J=7.1 Hz, 3H), 1.27 (d, J=6.8 Hz, 0.4H), 1.32-1.41 (m, 3H), 1.41-1.54 (m, 2H), 1.46 (d, J=7.1 Hz, 2.6H), 1.55-1.66 (m, 2H), 1.67-1.84 (m, 6H), 1.98-2.11 (m, 3H), 2.22-2.32 (m, 1H), 2.45-2.55 (m, 3H), 2.62-2.68 (m, 1H), 3.06-3.18 (m, 4H), 3.35-3.47 (m, 1H), 3.49-3.60 (m, 1H), 3.73-3.85 (m, 1H), 3.92-4.01 (m, 2H), 4.02-4.11 (m, 1H), 6.19 (d, J=8.3 Hz, 1H), 7.40 (d, J=8.2 Hz, 2H), 7.45 (d, J=8.3 Hz, 2H), 7.60-7.67 (m, 4H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09365511B2 |
|---|
| Source dataset | uspto-grants-2016_06 |
|---|
| ORD ID | ord-0267909ec31341fba0fb97193bc2d064 |
|---|
| Source note | uspto-grants-2016_06 |
|---|
