HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoroacetic acid → 5-{[(1R,2S)-2-aminocyclohexyl]amino}-3-{[6-(piperazin-1-ylmethyl)pyridin-2-yl]amino}pyridine-2-carbonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | tert-butyl 4-[(6-{[5-({(1R,2S)-2-[(tert-butoxycarbonyl)amino]cyclohexyl}amino)-2-cyanopyridin-3-yl]amino}pyridin-2-yl)methyl]piperazine-1-carboxylate | HCID 86731739 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 5-{[(1R,2S)-2-aminocyclohexyl]amino}-3-{[6-(piperazin-1-ylmethyl)pyridin-2-yl]amino}pyridine-2-carbonitrile | HCID 86731740 | — |
Reaction Steps
To a solution of tert-butyl 4-[(6-{[5-({(1R,2S)-2-[(tert-butoxycarbonyl)amino]cyclohexyl}amino)-2-cyanopyridin-3-yl]amino}pyridin-2-yl)methyl]piperazine-1-carboxylate (90 mg, 0.15 mmol) in dichloromethane (1.5 mL) was added trifluoroacetic acid (0.17 mL, 2.2 mmol) and the reaction mixture was stirred for 1 hour at room temperature. The reaction was then concentrated under reduced pressure to afford 5-{[(1R,2S)-2-aminocyclohexyl]amino}-3-{[6-(piperazin-1-ylmethyl)pyridin-2-yl]amino}pyridine-2-carbonitrile. The material was used in the next step without further purification. MS ESI calc'd for C22H31N8 [M+H]+ 407. found 407.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09216173B2 |
| Source dataset | uspto-grants-2015_12 |
| ORD ID | ord-2ea29a686cea4c7bbc158d25ddabe59c |
| Source note | uspto-grants-2015_12 |