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-({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 | 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 | 3-amino-6-[1-(4-hydroxybutyl)-1H-pyrazol-4-yl]-N-methylpyridine-2-carboxamide | HCID 86697703 | — |
| Product | 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 | 40% |
Reaction Steps
Prepared analogously to Compound 1B using 3-amino-6-[1-(4-hydroxybutyl)-1H-pyrazol-4-yl]-N-methylpyridine-2-carboxamide (Compound 15C, 95 mg, 333 μmol) to afford 95 mg of the title compound (40%). 1H NMR (400 MHz, CD3OD) δ 8.98 (d, J=8.3 Hz, 1H), 8.42 (s, 1H), 8.28 (s, 1H), 8.20 (s, 1H), 7.76 (d, J=6.1 Hz, 1H), 7.64 (d, J=8.8 Hz, 1H), 7.01 (d, J=1.8 Hz, 1H), 6.90 (td, J=2.2, 8.1 Hz, 1H), 4.22 (t, J=7.1 Hz, 2H), 4.01-4.11 (m, 4H), 3.87 (s, 3H), 3.59 (t, J=6.4 Hz, 2H), 3.28-3.29 (m, 1H), 3.24 (s, 1H), 2.96 (s, 3H), 1.92-2.04 (m, 2H), 1.51-1.60 (m, 2H), 1.25 (t, J=7.1 Hz, 6H). MS (ESI): m/z 707.71 [M+H]+. UPLC: tR=1.25 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-de67462d33754910884f218cef0b0402 |
| Source note | uspto-grants-2015_09 |