HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ammonium Chloride → Tert-butyl cis-2-(5-aminocarbonyl-3-fluoro-6-(isoquinolin-4-ylamino)pyridin-2-ylamino)cyclohexylcarbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | 6-(cis-2-(Tert-butoxycarbonylamino)cyclohexylamino)-5-fluoro-2-(isoquinoline 4-ylamino)nicotinic acid | HCID 86683888 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | Tert-butyl cis-2-(5-aminocarbonyl-3-fluoro-6-(isoquinolin-4-ylamino)pyridin-2-ylamino)cyclohexylcarbamate | HCID 86683889 | 72.5% |
Reaction Steps
Ammonium chloride (28 mg), WSC.HCl (75 mg), HOBt.H2O (60 mg), and diisopropylethylamine (180 μl) were added to a DMF (1.3 ml) suspension containing 6-(cis-2-(tert-butoxycarbonylamino)cyclohexylamino)-5-fluoro-2-(isoquinoline 4-ylamino)nicotinic acid (65 mg), followed by stirring at room temperature for 3 hours. A saturated aqueous ammonium chloride solution and ethyl acetate were added to the reaction mixture. Solid matter was collected by filtration and washed with water and ethyl acetate, and a light yellow solid of tert-butyl cis-2-(5-aminocarbonyl-3-fluoro-6-(isoquinolin-4-ylamino)pyridin-2-ylamino)cyclohexylcarbamate (47 mg) was thus obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08772320B2 |
| Source dataset | uspto-grants-2014_07 |
| ORD ID | ord-ce3d70a12c5443b1b40295487ec72dfa |
| Source note | uspto-grants-2014_07 |