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-({2-(dimethylcarbamoyl)-4-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]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,N-dimethylbenzamide | HCID 67814803 | — |
| Product | Diethyl (4-{[4-({2-(dimethylcarbamoyl)-4-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]phenyl}amino)-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzyl)phosphonate | HCID 86697696 | 22% |
Reaction Steps
Prepared analogously to Compound 1B replacing Compound 1C with 2-Amino-5-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-N,N-dimethylbenzamide (Compound 11C, 506 mg, 1.19 mmol) to afford 177 mg of the title compound (22%). 1H NMR (400 MHz, CD3OD) δ 8.29 (s, 1H), 8.16 (s, 1H), 7.97 (s, 1H), 7.71-7.79 (m, 2H), 7.62 (d, J=1.8 Hz, 1H), 7.40 (d, J=7.8 Hz, 2H), 7.12 (d, J=5.6 Hz, 2H), 4.32 (t, J=6.9 Hz, 2H), 3.91-4.04 (m, 4H), 3.55-3.61 (m, 2H), 3.07-3.16 (d, J=21 Hz, 2H), 3.04 (s, 3H), 2.91 (s, 3H), 2.10 (t, J=6.4 Hz, 2H), 1.21 (t, J=7.1 Hz, 6H). MS (ESI): m/z 676.77 [M+H]+. UPLC: tR=1.07 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-0c81bdcb50c94942adb854e21e137af4 |
| Source note | uspto-grants-2015_09 |