Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 4-Thiazolecarboxylic acid | HCID 304271 | — |
| 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 86680280 | HCID 86680280 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 66840555 | HCID 66840555 | — |
Reaction Steps
To a mixture of compound 1d (0.15 mmol), thiazole-4-carboxylic acid 1e (23 mg, 0.18 mmol), and Et3N (0.09 mL, 0.65 mmol) in CH2Cl2 (3 mL) at room temperature was added HATU (68 mg, 0.18 mmol). The reaction mixture was stirred at room temperature for 18 h. It was diluted with diethyl ether, washed with aq. NaHCO3 and aq. NaCl, dried over Na2SO4, filtered, and concentrated. Purification by flash column chromatography (silica gel, 3% MeOH/CH2Cl2) gave compound 1. 1H NMR (400 MHz, CD3OD): δ 8.80 (d, J=2 Hz, 1H), 8.13 (t, J=0.8 Hz, 1H), 8.03 (d, J=2 Hz, 1H), 8.01 (d, J=8.6 Hz, 1H), 7.73 (dd, J=1.2 Hz, 8.6 Hz, 1H), 4.31 (m, 2H), 4.21 (m, 1H), 4.15 (m, 1H), 4.01 (m, 1H), 3.93 (m, 2H), 3.81 (m, 1H), 3.33 (m, 1H), 2.55-2.40 (m, 4H); MS m/z (M+H+) 515.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09375430B2 |
|---|
| Source dataset | uspto-grants-2016_06 |
|---|
| ORD ID | ord-5e5ee23b07084fa78117c0f20c61cc2b |
|---|
| Source note | uspto-grants-2016_06 |
|---|
