Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| 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 | (4-(Azetidin-3-yl)piperazin-1-yl)(thiazol-2-yl)methanone | HCID 59625677 | — |
| Reactant | HCID 59625841 | HCID 59625841 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 59626045 | HCID 59626045 | 20.8% |
Reaction Steps
To a mixture of compound 5e (71.6 mg, 0.22 mmol), compound 56d (53.1 mg, 0.2 mmol), and Et3N (0.14 mL, 1.0 mmol) in CH2Cl2 (1 mL) at room temperature was added HATU (106.5 mg, 0.28 mmol). The reaction mixture was stirred at room temperature overnight. The mixture was diluted with CH2Cl2 and H2O, washed with aqueous NaHCO3 and brine, dried over Na2SO4, filtered, and concentrated. Purification of the residue by flash column chromatography (silica gel, 2-4% MeOH/EtOAc) gave compound Cpd 753 (20.8 mg). 1H NMR (400 MHz, CDCl3): δ 7.89 (d, J=2.4 Hz, 1H), 7.74 (s, 1H), 7.55 (d, J=2.7 Hz, 1H), 7.49 (d, J=8.3 Hz, 1H), 7.15-7.35 (m, 6H), 6.89 (s, 1H), 4.06-4.60 (m, 8H), 3.79-3.98 (m, 2H), 3.78 (s, 3H), 3.17-3.31 (m, 1H), 2.35-2.64 (m, 4H). MS m/z (M+H+) 500.3.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08691805B2 |
|---|
| Source dataset | uspto-grants-2014_04 |
|---|
| ORD ID | ord-aeae5f3748e84d6dabea185b7fae4507 |
|---|
| Source note | uspto-grants-2014_04 |
|---|
