HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 3-[5-Cyano-6-[(2,2-dimethyl-propyl)-methyl-amino]-2-(pyrrolidin-3-ylamino)-pyrimidin-4-ylamino]-N-methoxy-4-methyl-benzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | (R)-(+)-1-Boc-3-aminopyrrolidine | HCID 854070 | — |
| Reactant | 3-{5-Cyano-6-[(2,2-dimethyl-propyl)-methyl-amino]-2-methanesulfinyl-pyrimidin-4-ylamino}-N-methoxy-4-methyl-benzamide | HCID 58928503 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 3-[5-Cyano-6-[(2,2-dimethyl-propyl)-methyl-amino]-2-(pyrrolidin-3-ylamino)-pyrimidin-4-ylamino]-N-methoxy-4-methyl-benzamide | HCID 72465904 | — |
Reaction Steps
3-{5-Cyano-6-[(2,2-dimethyl-propyl)-methyl-amino]-2-methanesulfinyl-pyrimidin-4-ylamino}-N-methoxy-4-methyl-benzamide (33 mg) and 1-N-Boc-3-(R)-aminopyrrolidine (30 mg), DIEA (0.2 mL) and p-dioxane (2 mL) were heated in a sealed tube at 75° C. for overnight. After the removal of the solvent in vacuo, the product was purified by silica gel column chromatography and treated with TFA/DCM (1:1) in order to remove the Boc-group. The product was then converted to hydrochloride salt by treating it with hydrochloric acid (1 M in ether) (Yield: 20 mg). MS (m/z): 567 (M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08044040B2 |
| Source dataset | uspto-grants-2011_10 |
| ORD ID | ord-90cad3a4b61d43e7bf4e82c11aa5395c |
| Source note | uspto-grants-2011_10 |