Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Morpholine | HCID 8083 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | 2-(5-Methyl-2-nitrophenyl)acetic acid | HCID 14740976 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Dichloromethane methanol | HCID 21226129 | — |
| Product | HCID 59394964 | HCID 59394964 | 87% |
Reaction Steps
2-(5-Methyl-2-nitro-phenyl)acetic acid (250 mg, 1.28 mmol) and HATU (443 mg, 1.17 mmol) were suspended in dichloromethane (5 mL) and treated with triethylamine (162 μL, 1.17 mmol) and morpholine (112 μL, 1.28 mmol). The solution was heated at 40° C. for 10 min. The reaction was washed with 1 N HCl and saturated sodium bicarbonate solution, dried over Na2SO4, filtered and concentrated in vacuo. Silica gel chromatography (1-10% methanol/dichloromethane) provided 2-(5-methyl-2-nitro-phenyl)-1-morpholino-ethanone as a white solid (267 mg, 87% yield). LC/MS m/z 265.0 [M+H]+. 1H NMR (400.0 MHz, DMSO-d6) S 7.97 (d, J=8.3 Hz, 1H), 7.33 (dd, J=1.3, 8.3 Hz, 1H), 7.27 (s, 1H), 4.10 (s, 2H), 3.66-3.64 (m, 2H), 3.59-3.54 (m, 4H), 3.43-3.41 (m, 2H), 2.39 (s, 3H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08633189B2 |
|---|
| Source dataset | uspto-grants-2014_01 |
|---|
| ORD ID | ord-8eb2e9c2a3254596987dc9d54f310500 |
|---|
| Source note | uspto-grants-2014_01 |
|---|
