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 (3-fluoro-4-{[4-({6-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-2-(methylcarbamoyl)pyridin-3-yl}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 | 3-amino-6-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-N-methylpyridine-2-carboxamide | HCID 67818794 | — |
| 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 | Diethyl (4-{[4-chloro-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-fluorobenzyl)phosphonate | HCID 86697719 | — |
| Product | diethyl (3-fluoro-4-{[4-({6-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-2-(methylcarbamoyl)pyridin-3-yl}amino)-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzyl)phosphonate | HCID 86697718 | 23% |
Reaction Steps
Prepared analogously to Compound 1B replacing compound 1C with Compound 6C (278 mg, 1.01 mmol) and Compound 1 E with diethyl (4-{[4-chloro-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-fluorobenzyl)phosphonate (Compound 22C, 446 mg, 1.01 mmol) to afford 157 mg of the title compound (23%). 1H NMR (400 MHz, CD3OD) δ=8.61-8.86 (m, 1H), 8.56 (s, 1H), 8.43 (br. s., 1H), 8.35 (s, 1H), 7.76 (d, J=8.8 Hz, 1H), 7.55 (t, J=8.0 Hz, 1H), 7.37 (dd, J=2.2, 11.0 Hz, 1H), 7.32 (d, J=8.3 Hz, 1H), 4.32 (t, J=7.0 Hz, 2H), 4.12 (quin, J=7.3 Hz, 4H), 3.57 (t, J=6.1 Hz, 2H), 3.42 (d, J=21.0 Hz, 2H), 3.00 (s, 3H), 2.11 (quin, J=6.5 Hz, 2H), 1.17-1.34 (m, 6H). MS (ESI): m/z=681.74 [M+H]+. UPLC: tR=1.20 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-a452e19c425f4c4fba0cbc55330ea2ff |
| Source note | uspto-grants-2015_09 |