HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethyl hydrogen (4-{[4-({2-(diethylcarbamoyl)-4-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]phenyl}amino)-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate → Ethyl hydrogen (4-{[4-({6-[1-(4-hydroxybutyl)-1H-pyrazol-4-yl]-2-(methylcarbamoyl)pyridin-3-yl}amino)-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethyl hydrogen (4-{[4-({2-(diethylcarbamoyl)-4-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]phenyl}amino)-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate | HCID 86697678 | — |
| Reactant | diethyl (4-{[4-({6-[1-(4-hydroxybutyl)-1H-pyrazol-4-yl]-2-(methylcarbamoyl)pyridin-3-yl}amino)-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate | HCID 86697702 | — |
| Product | Ethyl hydrogen (4-{[4-({6-[1-(4-hydroxybutyl)-1H-pyrazol-4-yl]-2-(methylcarbamoyl)pyridin-3-yl}amino)-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate | HCID 86697701 | 103.2% |
Reaction Steps
Prepared analogously to Compound 3A using diethyl (4-{[4-({6-[1-(4-hydroxybutyl)-1H-pyrazol-4-yl]-2-(methylcarbamoyl)pyridin-3-yl}amino)-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate (Compound 15B, 95 mg, 0.13 mmol) to afford 91 mg of the title compound (99%). 1H NMR (400 MHz, CD3OD) δ 8.96 (d, J=6.1 Hz, 1H), 8.50 (s, 1H), 8.29 (s, 1H), 8.20 (s, 1H), 7.69 (d, J=9.1 Hz, 2H), 7.10 (s, 1H), 6.93 (dd, J=2.0, 8.1 Hz, 1H), 4.24 (t, J=6.9 Hz, 2H), 3.83-3.91 (m, 5H), 3.60 (t, J=6.4 Hz, 2H), 2.99-3.06 (m, 2H), 2.98 (s, 3H), 1.94-2.04 (m, 2H), 1.51-1.61 (m, 2H), 1.16 (t, J=7.1 Hz, 3H). MS (ESI): m/z 679.80 [M+H]+. UPLC: tR=1.11 min (UPLC-SQD: analytical—2 min).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09133224B2 |
| Source dataset | uspto-grants-2015_09 |
| ORD ID | ord-b6808a7c041f42bc9120c6027bf88f41 |
| Source note | uspto-grants-2015_09 |