HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → Ammonia
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Pyrazolo[1,5-a]pyrimidine-3-carboxylic acid | HCID 1910189 | — |
| 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 | 3-Methyl-4-{[(3S)-3-methyl-1-piperazinyl]sulfonyl}benzonitrile | HCID 59152067 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | Ammonia | HCID 222 | — |
| Product | HCID 59152092 | HCID 59152092 | — |
Reaction Steps
To a solution of 3-methyl-4-{[(3S)-3-methyl-1-piperazinyl]sulfonyl}benzonitrile (may be prepared as described in Description 9) (75 mg, 0.268 mmol), pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (48.2 mg, 0.295 mmol) and DIPEA (0.070 ml, 0.403 mmol) in dry DMF (3 ml) at rt under argon was added HATU (122 mg, 0.322 mmol) and the resulting yellow solution stirred at rt for 1 hour. Concentration in vacuo gave a yellow oil, that was purified by MDAP; concentration of the desired fractions gave a clear film (80.2 mg). Flash chromatography (silica; Flash 12S; linear gradient (1-8%) [2M NH3 in MeOH] in DCM) gave the title compound as a clear film (44.9 mg), that became a white solid on standing in vacuo (1 mbar) for 1 h.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08093249B2 |
| Source dataset | uspto-grants-2012_01 |
| ORD ID | ord-3fb47c3eb07a420e9b28416c87579ac5 |
| Source note | uspto-grants-2012_01 |