Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | HCID 118890590 | HCID 118890590 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Methanol--water (1/1) | HCID 22242641 | — |
| Product | HCID 56968328 | HCID 56968328 | 46.2% |
Reaction Steps
To a solution of 2-(3,5-dichloro-phenylamino)-1-(3-{methyl-[7-(tosyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-amino}-azepan-1-yl)-ethanone (235 mg. 0.39 mmol) in MeOH:H2O (4:1, 5 mL) was added K2CO3 (216 mg, 1.56 mmol) and heated at 90° C. for 1 h. The reaction mixture was cooled to rt and concentrated in vacuo to give a residue which was subjected to column chromatography (silica gel, gradient MeOH in CH2Cl2) to afford the titled compound (80.6 mg, 46%). 1H NMR (DMSO-d6, 400 MHz): 11.60 (1s, 1H), 8.08 (s, 1H), 7.12 (d, J=4 Hz, 1H), 6.72 (s, 1H), 6.69 (s, 1H), 6.63 (s, 1H), 6.62 (s, 1H), 6.38-6.35 (m, 1H), 4.98-4.85 (m, 1H), 4.29 and 1.28 (2d, J=2.1 Hz, 1H), 4.10-3.88 (m, 3H), 3.65-2.32 (m, 2H), 3.17 (s, 3H), 1.93-1.76 (m, 6H). LC-MS: m/z [M+1]=447.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09273028B2 |
|---|
| Source dataset | uspto-grants-2016_03 |
|---|
| ORD ID | ord-d3a3c7c8db12425b9b92ec2d28aea943 |
|---|
| Source note | uspto-grants-2016_03 |
|---|