Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Tert-butyl 4-hydroxypiperidine-1-carboxylate | HCID 643502 | — |
| Reactant | Potassium tert-butoxide | HCID 23665647 | — |
| Reactant | HCID 59652010 | HCID 59652010 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Solvent | tert-Butanol | HCID 6386 | — |
| Product | HCID 59651905 | HCID 59651905 | 54.5% |
Reaction Steps
A solution of 5-(6-chloropyridin-3-yl)-2H-pyridazin-3-one (73 mg, 0.35 mmol) and 4-hydroxypiperidine-1-carboxylic acid tert-butyl ester (140 mg, 0.70 mmol) in 2.7 mL of DMSO was stirred as KOtBu in 2-methyl-2-propanol (1.0 M, 14.4 mL) was added dropwise. After stirring at 110° C. overnight, the reaction was cooled to rt, and 2 mL of water was added. The mixture was extracted with CH2Cl2 (3×10 mL), the extracts combined and dried over Na2SO4. The crude product was purified by prep. TLC with 10% MeOH in CH2Cl2 to give 71 mg (54%) of 4-[5-(6-oxo-1,6-dihydropyridazin-4-yl)-pyridin-2-yloxy]piperidine-1-carboxylic acid tert-butyl ester; MS m/z 273 (M-Boc-H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08207168B2 |
|---|
| Source dataset | uspto-grants-2012_06 |
|---|
| ORD ID | ord-cd1c7a1e0711481d9cf559d14afa7713 |
|---|
| Source note | uspto-grants-2012_06 |
|---|
