Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | HCID 86683663 | HCID 86683663 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 53261683 | HCID 53261683 | 30% |
Reaction Steps
Tert-butyl (1-(4-(1-methyl-2-oxo-7-(thiophen-3-yl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutyl)carbamate (25 mg, 0.051 mmol) was dissolved in dichloromethane (0.5 ml); this solution was added to a scx-2 catch and release cartridge (5 g), precalibrated using methanol (15 ml) and dichloromethane (15 ml). After allowing binding for 12 hours, the column was washed with methanol (6 ml), then the product eluted with 7M ammonia in methanol (4×2 ml). The combined product fractions were concentrated to dryness under reduced pressure to give the desired product as a white solid (5.8 mg, 30% yield). LCMS (Method D): RT=0.777 min, M+1=393. 1H-NMR (500 MHz, CD3OD) δ 7.35-7.29 (3H, m), 7.28-7.25 (1H, dd), 7.21-7.18 (1H, s), 7.17-7.14 (1H, dd), 7.07-7.03 (1H, dd), 6.71-6.67 (1H, dd), 4.80 (2H, s), 3.32 (3H, s), 2.51-2.37 (4H, m), 2.25-2.13 (1H, m).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09221838B2 |
|---|
| Source dataset | uspto-grants-2015_12 |
|---|
| ORD ID | ord-1f6f4a842e144cb5a0cb8a234e13f844 |
|---|
| Source note | uspto-grants-2015_12 |
|---|