HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 1-{6-[2-(methoxymethyl)-4-methyl-1H-benzo[d]imidazol-6-yloxy]pyrimidin-4-yl}spiro-(piperidin-4,4'-pyrido[2,3-d][1,3]oxazin)-2'(1'H)-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Spiro[piperidine-4,4'-pyrido[2,3-d][1,3]oxazin]-2'(1'H)-one hydrochloride | HCID 66687106 | — |
| Reactant | 6-(6-chloropyrimidin-4-yloxy)-2-(methoxymethyl)-4-methyl-1H-benzo[d]imidazole | HCID 86663913 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 1-{6-[2-(methoxymethyl)-4-methyl-1H-benzo[d]imidazol-6-yloxy]pyrimidin-4-yl}spiro-(piperidin-4,4'-pyrido[2,3-d][1,3]oxazin)-2'(1'H)-one | HCID 46244759 | — |
Reaction Steps
49 mg (0.19 mmol) spiro[piperidin-4,4′-pyrido[2,3-d][1,3]oxazin]-2′(1′H)-one hydrochloride, 50 mg (0.16 mmol) 6-(6-chloropyrimidin-4-yloxy)-2-(methoxymethyl)-4-methyl-1H-benzo-[d]imidazole and 0.10 mL (0.57 mmol) DIPEA in 2.0 mL DMF were stirred at 40° C. over the weekend. The reaction mixture was purified by preparative HPLC-MS. The fractions containing product were partially evaporated down i.vac. and neutralised with 4M sodium hydroxide solution. The precipitate formed was suction filtered, washed and dried.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08952014B2 |
| Source dataset | uspto-grants-2015_02 |
| ORD ID | ord-6103fdbcb5774a52b6d8af4880aa60d1 |
| Source note | uspto-grants-2015_02 |