HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → HCID 121434541, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| 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 117858300 | HCID 117858300 | — |
| Reactant | HCID 117859510 | HCID 117859510 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 121434541 | HCID 121434541 | 55.2% |
Reaction Steps
A mixture of 52 mg of 7-[(2,6-difluorobenzyl)oxy]-2,5-dimethylpyrazolo[1,5-a]pyridine-3-carboxylic acid (75% purity, 0.118 mmol) from Example 4A, 72 mg of HATU (0.188 mmol) and 0.138 ml (0.792 mmol) of N,N-diisopropylethylamine in 0.7 ml of DMF was stirred at RT for 10 min. Subsequently, 53 mg (0.236 mmol) of methyl 3-(aminomethyl)adamantane-1-carboxylate from Example 37A in 0.5 ml of DMF were added and the mixture was stirred at RT overnight. The reaction mixture was admixed with water and acetonitrile and purified by means of preparative HPLC (RP18 column, eluent:acetonitrile/water gradient with addition of 0.05% formic acid). 35 mg of the target compound were obtained (53% of theory).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09422285B2 |
| Source dataset | uspto-grants-2016_08 |
| ORD ID | ord-8c281e583bf4455d9aaef87017a3a98c |
| Source note | uspto-grants-2016_08 |