HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → HCID 178517415, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Oxalyl chloride | HCID 65578 | — |
| Reactant | 1-(Trifluoromethyl)cyclopropane-1-carboxylic acid | HCID 2778306 | — |
| Reactant | Pyridine methylene chloride | HCID 21875418 | — |
| Reactant | 2-(1-(2,3-difluorobenzyl)-5-(isoxazol-3-yl)-1H-pyrazol-3-yl)pyrimidine-4,5-diamine hydrochloride | HCID 89657291 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | Ammonium Chloride | HCID 25517 | — |
| Product | HCID 178517415 | HCID 178517415 | 36% |
Reaction Steps
To a solution of 1-(trifluoromethyl)cyclopropanecarboxylic acid (0.159 g, 1.03 mmol) in DCM was added oxalyl chloride (0.081 ml, 0.928 mmol) and catalytic DMF. Once gas evolution ceased, this crude reaction mixture was added portion-wise to a suspension of 2-(1-(2,3-difluorobenzyl)-5-(isoxazol-3-yl)-1H-pyrazol-3-yl)pyrimidine-4,5-diamine hydrochloride (Compound 8, 40 mg, 0.100 mmol) in dichloromethane/pyridine (2 ml/2 ml) until complete consumption of starting material was observed by LS/MS. After an ammonium chloride (saturated aqueous) and dichloromethane workup, column chromatography (0-10% MeOH/DCM) provided the desired product as an off-white solid (36%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09139564B2 |
| Source dataset | uspto-grants-2015_09 |
| ORD ID | ord-e8aa27534d3146e8a56508b79a183f86 |
| Source note | uspto-grants-2015_09 |