Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| 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 58032656 | HCID 58032656 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 58032594 | HCID 58032594 | — |
Reaction Steps
The reaction was carried out under argon. (7R)-7-(4-Cyanophenyl)-5-methyl-4-[3-(trifluoromethyl)phenyl]-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylic acid (62 mg, 145 μmol) and ammonium chloride (116.7 mg, 2.2 mmol, 15 eq.) were initially charged in dry DMF (3.5 ml) at 0° C., and HATU (415 mg, 1.8 mmol, 7.5 eq.) and triethylamine (147 mg, 1.45 mmol, 10 eq.) were added. The mixture was stirred for 12 h, during which time it gradually warmed to RT. The reaction mixture was then concentrated, and the residue was taken up in acetonitrile (with 0.1% TFA) and then purified by preparative HPLC (Gromsil C18 column, 10 μm; mobile phase: acetonitrile/water+0.1% TFA 10:90→90:10). The product was obtained as a colorless amorphous solid (36 mg, 58% of theory).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09359362B2 |
|---|
| Source dataset | uspto-grants-2016_06 |
|---|
| ORD ID | ord-aa2842c0802f459e9d0379364f848438 |
|---|
| Source note | uspto-grants-2016_06 |
|---|
