HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diethyl (4-{[4-({7-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-4-yl}amino)-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate → Diethyl (4-{[4-({4-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-2-(methylcarbamoyl)phenyl}amino)-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzyl)phosphonate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diethyl (4-{[4-({7-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-4-yl}amino)-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate | HCID 58292892 | — |
| Reactant | 2-amino-5-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-N-methylbenzamide | HCID 67814054 | — |
| Reactant | Diethyl (4-{[4-chloro-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzyl)phosphonate | HCID 86654003 | — |
| Product | Diethyl (4-{[4-({4-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-2-(methylcarbamoyl)phenyl}amino)-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzyl)phosphonate | HCID 86697690 | 68% |
Reaction Steps
Prepared analogously to Compound 1B replacing Compound 1E with Compound 2C and replacing Compound 1C with 2-amino-5-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-N-methylbenzamide (Compound 8C, 517 mg, 1.22 mmol) to afford 550 mg of the title compound (68%). 1H NMR (400 MHz, CD3OD) δ 8.36 (br. s., 1H), 8.32 (s, 1H), 8.18 (s, 1H), 8.00 (s, 1H), 7.91 (d, J=2.0 Hz, 1H), 7.69 (dd, J=2.0, 8.8 Hz, 1H), 7.47 (d, J=8.1 Hz, 2H), 7.35 (dd, J=2.4, 8.5 Hz, 2H), 4.31 (t, J=6.9 Hz, 2H), 3.98-4.10 (m, 4H), 3.57 (t, J=6.1 Hz, 2H), 3.26 (s, 2H), 2.92 (s, 3H), 2.10 (t, J=6.4 Hz, 2H), 1.23 (t, J=7.1 Hz, 6H). MS (ESI): m/z: 662.74 [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-1bdaa953c368422583aa9b62666401f3 |
| Source note | uspto-grants-2015_09 |