HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-((2-Chloro-5-(trifluoromethyl)pyrimidin-4-yl)amino)-N-methylbenzamide → Bis(2-methoxyethyl) (3-methoxy-4-{[4-{[2-(methylcarbamoyl)phenyl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzyl)phosphonate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-((2-Chloro-5-(trifluoromethyl)pyrimidin-4-yl)amino)-N-methylbenzamide | HCID 86633861 | — |
| Reactant | Bis(2-methoxyethyl)(4-amino-3-methoxybenzyl)phosphonate | HCID 86654042 | — |
| Product | Bis(2-methoxyethyl) (3-methoxy-4-{[4-{[2-(methylcarbamoyl)phenyl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzyl)phosphonate | HCID 58292963 | 61.7% |
Reaction Steps
The title compound was prepared according to Example 102 using 2-{[2-chloro-5-(trifluoromethyl)pyrimidin-4-yl]amino}-N-methylbenzamide (Compound 104A, 50.0 mg, 0.15 mmol) and bis(2-methoxyethyl)(4-amino-3-methoxybenzyl)phosphonate (Compound 217C, 55.4 mg, 0.17 mmol). 58.1 mg (61%) of the desired product obtained after purification. 1H NMR (400 MHz, MeOD) δ ppm 8.24-8.35 (m, 2H), 7.95 (d, J=8.08 Hz, 1H), 7.62 (dd, J=7.83, 1.52 Hz, 1H), 7.46 (ddd, J=8.53, 7.39, 1.52 Hz, 1H), 7.16 (td, J=7.58, 1.01 Hz, 1H), 6.96 (t, J=2.02 Hz, 1H), 6.72-6.80 (m, 1H), 4.05-4.16 (m, 4H), 3.87 (s, 3H), 3.50-3.57 (m, 4H), 3.33 (s, 6H), 3.20-3.29 (m, 2H), 2.89 (s, 3H). MS (ES+): m/z 628.16/629.20 (100/98) [MH+]. HPLC: tR=1.39 min (Micromass TOF: polar—3 min).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08399433B2 |
| Source dataset | uspto-grants-2013_03 |
| ORD ID | ord-c3add16c106e469c8900aab03d9ebf35 |
| Source note | uspto-grants-2013_03 |