HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 4-[4-((1R,2R)-2-amino-cyclopentyloxy)-5-trifluoromethyl-pyrimidin-2-ylamino]-3-methoxy-N-(1-methyl-piperidin-4-yl)-benzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | rac-(1R,2R)-2-aminocyclopentan-1-ol | HCID 10464306 | — |
| Reactant | 4-(4-chloro-5-trifluoromethyl-pyrimidin-2-ylamino)-3-methoxy-N-(1-methyl-piperidin-4-yl)-benzamide | HCID 58200916 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 4-[4-((1R,2R)-2-amino-cyclopentyloxy)-5-trifluoromethyl-pyrimidin-2-ylamino]-3-methoxy-N-(1-methyl-piperidin-4-yl)-benzamide | HCID 58450897 | — |
Reaction Steps
(R,R)-2-aminocyclopentanol×HCl (155 mg) is added to a suspension of NaH (135.2 mg) in dioxane (0.75 mL) and stirred for 30 min at RT. Then 4-(4-chloro-5-trifluoromethyl-pyrimidin-2-ylamino)-3-methoxy-N-(1-methyl-piperidin-4-yl)-benzamide (250 mg) is added. After 18 h, H2O (50 mL) is added. The precipitate formed is filtered off, washed with H2O, dissolved in CH2Cl2 and extracted with aqueous KHSO4 solution (10%). The aqueous phase is made basic again with K2CO3 and extracted with CH2Cl2. The organic phase is dried on magnesium sulphate, filtered to remove the desiccant and the solvent is eliminated in vacuo.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08466155B2 |
| Source dataset | uspto-grants-2013_06 |
| ORD ID | ord-0188558b097749a9afef32a261f7895e |
| Source note | uspto-grants-2013_06 |