HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,2-Dimethoxyethane → HCID 68695049, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,2-Dimethoxyethane | HCID 8071 | — |
| Reactant | 4-Hydroxybutanenitrile | HCID 220705 | — |
| Reactant | Potassium tert-butoxide | HCID 23665647 | — |
| Reactant | 4-(7-Fluoro-quinazolin-4-yl)-piperidine-1-carboxylic acid tert-butyl ester | HCID 59551736 | — |
| Solvent | Propan-2-one--dichloromethane (1/1) | HCID 21584124 | — |
| Product | HCID 68695049 | HCID 68695049 | 42% |
Reaction Steps
A mixture of 4-hydroxybutyronitrile (24.2 mg, 285 μmol) [Organometallics (1996), 15(4), 1236-41], KOtBu (34.8 mg, 311 μmol), and DME was stirred at rt, followed by the addition of 4-(7-Fluoro-quinazolin-4-yl)-piperidine-1-carboxylic acid tert-butyl ester (48.8 mg, 147 μmol) (prepared as described in Example 65b). The resulting homogeneous solution was stirred at rt for 2 hr, and was then directly loaded onto a 5 g Jones silica cartridge pre-equilibrated with 9:1 DCM/acetone, and eluted with 9:1→8:2 DCM/acetone to afford the title intermediate (24.5 mg, 42%) as a colorless oil. LC/MS (ESI) calcd mass 396.2, found 397.1 (MH)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08071768B2 |
| Source dataset | uspto-grants-2011_12 |
| ORD ID | ord-58b1eee3603546b78f50955a6ba68eaf |
| Source note | uspto-grants-2011_12 |