HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylamine → 6-[cyclohexyl(cyclopropylmethyl)amino]-N-(4-{[(2-methoxyethyl)amino]sulfonyl}-2-methylphenyl)pyrimidine-4-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylamine | HCID 7912 | — |
| Reactant | N-(cyclopropylmethyl)cyclohexanamine | HCID 1531432 | — |
| Reactant | 6-chloro-N-(4-(N-(2-methoxyethyl)sulfamoyl)-2-methylphenyl)pyrimidine-4-carboxamide | HCID 59447107 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | 6-[cyclohexyl(cyclopropylmethyl)amino]-N-(4-{[(2-methoxyethyl)amino]sulfonyl}-2-methylphenyl)pyrimidine-4-carboxamide | HCID 59446971 | 84.3% |
Reaction Conditions
| Temperature | 160 °C |
|---|
Reaction Steps
A solution of 6-chloro-N-(4-(N-(2-methoxyethyl)sulfamoyl)-2-methylphenyl)pyrimidine-4-carboxamide (Intermediate 38, 100 mg; 0.26 mmol) and diisopropylamine (91 mL; 0.52 mmol) in ethanol (2.5 ml) was treated with N-(cyclopropylmethyl)cyclohexanamine (54.4 mg; 0.33 mmol). The mixture was heated to 160° C. in a microwave for 1 hour and the solvent removed in vacuo. The residue was purified by column chromatography (silica) eluting with petroleum ether containing increasing amounts of EtOAc to give the title compound as a white solid (110 mg, 84%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09150519B2 |
| Source dataset | uspto-grants-2015_10 |
| ORD ID | ord-94868dfe55ed44e29d4a03c3b6f1d15f |
| Source note | uspto-grants-2015_10 |