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-(3-hydroxypropyl)-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-(3-hydroxypropyl)-1H-pyrazol-4-yl]-N-methylpyridine-2-carboxamide | HCID 67818794 | — |
| Product | Diethyl (4-{[4-({6-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-2-(methylcarbamoyl)pyridin-3-yl}amino)-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate | HCID 86697685 | 68% |
Reaction Steps
Prepared analogously to Compound 1B replacing Compound 1C with 3-amino-6-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-N-methylpyridine-2-carboxamide (Compound 6C, 220.0 mg, 0.7991 mmol) to afford 337 mg of the title compound (68%). 1H NMR (400 MHz, CDCl3) δ 12.19 (s, 1H), 9.04 (d, J=9.1 Hz, 1H), 8.36-8.44 (m, 2H), 8.21 (s, 1H), 8.08 (s, 1H), 8.04 (br. s., 1H), 7.63 (d, J=8.8 Hz, 1H), 7.52 (s, 1H), 6.95 (td, J=2.3, 8 Hz, 1H), 6.86 (t, J=1.9 Hz, 1H), 4.40 (t, J=6.2 Hz, 2H), 3.97-4.11 (m, 4H), 3.91 (s, 3H), 3.65 (q, J=5.3 Hz, 2H), 3.18 (d, J=21.1 Hz, 2H), 3.09 (d, J=5.1 Hz, 3H), 2.11 (quin, J=5.9 Hz, 2H), 1.26 (t, J=7.1 Hz, 6H) [OH proton obscured]. MS (ES+): m/z 693.75 [M+H]+. UPLC: tR=1.24 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-5683cb7ece524f14a9d1770dac344a48 |
| Source note | uspto-grants-2015_09 |