Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 2-[4-(Trifluoromethoxy)phenyl]acetic acid | HCID 2777319 | — |
| 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 | 1-(4-fluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine | HCID 67984610 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 73335727 | HCID 73335727 | 95.4% |
Reaction Steps
To a mixture of 1-(4-fluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine (0.023 g, 0.10 mmol), 4-(trifluoromethoxy)phenylacetic acid (0.025 g, 0.11 mmol) and Et3N (0.060 mL, 0.43 mmol) in DMF (0.6 mL) was added HATU (0.060 g, 0.15 mmol). The mixture was stirred at rt for 30 min. It was then quenched with water. The mixture was partitioned between EtOAc (50 mL) and sat. NaHCO3 (30 mL). The organic layer was separated, dried over Na2SO4, concentrated in vacuo, and purified by reverse phase HPLC to afford the desired product (0.040 g, 95%). 1H NMR (400 MHz, CDCl3) δ 8.51 (s, 1H), 7.43 (m, 2H), 7.30 (m, 2H), 7.18 (m, 4H), 3.91 (s, 2H), 3.76 (m, 2H), 2.79 (t, J=6.4 Hz, 2H), 2.00 (m, 2H); MS: (ES) m/z calculated for C21H17F4N3O2 [M+H]+ 420.1, found 420.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09181241B2 |
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| Source dataset | uspto-grants-2015_11 |
|---|
| ORD ID | ord-c903bd84c77f4d75b2f8d577b6579a75 |
|---|
| Source note | uspto-grants-2015_11 |
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