HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,2-Difluoro-4-(methylsulfonyl)benzene → 2,3-difluoro-4-(2-oxo-4-(1-(5-propylpyrimidin-2-yl)piperidin-4-yloxy)pyridin-1(2H)-yl)benzonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,2-Difluoro-4-(methylsulfonyl)benzene | HCID 2782743 | — |
| Reactant | 4-(1-(5-propylpyrimidin-2-yl)piperidin-4-yloxy)pyridin-2(1H)-one | HCID 67072517 | — |
| Reactant | 4-(1-(5-ethylpyrimidin-2-yl)piperidin-4-yloxy)pyridin-2(1H)-one | HCID 67367294 | — |
| Product | 2,3-difluoro-4-(2-oxo-4-(1-(5-propylpyrimidin-2-yl)piperidin-4-yloxy)pyridin-1(2H)-yl)benzonitrile | HCID 57468457 | — |
Reaction Steps
Example 253 was prepared according to procedures described in Example 248 substituting 4-(1-(5-propylpyrimidin-2-yl)piperidin-4-yloxy)pyridin-2(1H)-one (prepared according to procedures described in Example 173 Step C) for 4-(1-(5-ethylpyrimidin-2-yl)piperidin-4-yloxy)pyridin-2(1H)-one and substituting 2,3,4-trifluorobenzonitrile (Oakwood) for 1,2-difluoro-4-(methylsulfonyl)benzene. 1H NMR (400 MHz, CDCl3) δ ppm 8.10 (s, 2 H), 7.35-7.53 (m, 1 H), 7.21-7.35 (m, 1H), 7.03 (d, J=7.03 Hz, 1 H), 6.01 (dd, J=7.65, 2.64 Hz, 1 H), 5.93 (d, J=2.51 Hz, 1 H), 4.43-4.54 (m, 1 H), 4.05-4.19 (m, 2 H), 3.50-3.66 (m, 2 H), 2.34 (t, J=7.53 Hz, 2 H), 1.93-2.11 (m, 2 H), 1.72-1.83 (m, 2 H), 1.42-1.56 (m, 2 H), 0.87 (t, J=7.28 Hz, 3 H). MS (ESI) 452 (M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08513424B2 |
| Source dataset | uspto-grants-2013_08 |
| ORD ID | ord-0b23abd215fe45aabcd494b037d7932b |
| Source note | uspto-grants-2013_08 |