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-[5-cyano-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 | 11-ethoxy-N-methyl-21-(trifluoromethyl)-10-oxa-4,5,17,19,23,26,29-heptaaza-11-phosphapentacyclo[22.2.2.213,16.12,5.118,22]dotriaconta-1(26),2(32),3,13,15,18(29),19,21,24,27,30-undecaene-25-carboxamide 11-oxide | HCID 76518268 | — |
| Reactant | 3-amino-6-[5-cyano-1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-N-methylpyridine-2-carboxamide | HCID 86697796 | — |
| Product | diethyl (4-{[4-({6-[5-cyano-1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-2-(methylcarbamoyl)pyridin-3-yl}amino)-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate | HCID 86697795 | 55% |
Reaction Steps
Prepared analogously to Compound 1B using diethyl (4-{[4-chloro-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate (Compound 1 E, 218 mg, 0.480 mmol) and 3-amino-6-[5-cyano-1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-N-methylpyridine-2-carboxamide (Compound 53C, 151 mg, 0.504 mmol) to afford 191 mg of the title compound (55%). 1H NMR (400 MHz, CD3OD) δ 9.19 (br. s., 1H), 8.47 (s, 1H), 8.38 (s, 1H), 7.91 (d, J=8.8 Hz, 1H), 7.69 (br. s., 1H), 7.08 (s, 1H), 6.98 (d, J=7.8 Hz, 1H), 4.52 (t, J=6.9 Hz, 2H), 4.01-4.14 (m, 3H), 3.88 (s, 2H), 3.61 (t, J=6.1 Hz, 2H), 3.36 (s, 2H), 2.99 (s, 3H), 2.17 (quin, J=6.5 Hz, 2H), 1.18-1.31 (m, 8H). MS (ESI): m/z=718.56 [M+H]+. UPLC: tR=1.36 min (UPLC-TOF: polar—2 min).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09133224B2 |
| Source dataset | uspto-grants-2015_09 |
| ORD ID | ord-854fbe495a594e7286d25747b5246df0 |
| Source note | uspto-grants-2015_09 |