HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diethyl cyanophosphonate → n-(4-(5-((Benzyl(methyl)amino)methyl)-1-(2,6-difluorobenzyl)-3-(4-(1-hydroxy-1-methylethyl)phenyl)-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidin-6-yl)phenyl)-n'-methoxyurea
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diethyl cyanophosphonate | HCID 76257 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Sodium ethoxide | HCID 2723922 | — |
| Reactant | 2-(4-Aminophenyl)propan-2-ol | HCID 9543261 | — |
| Reactant | 4-((Benzyl(methyl)amino)methyl)-2-((2,6-difluorobenzyl)(ethoxycarbonyl)amino)-5-(4-(3-methoxyureido)phenyl)thiophene-3-carboxylic acid | HCID 18324800 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | n-(4-(5-((Benzyl(methyl)amino)methyl)-1-(2,6-difluorobenzyl)-3-(4-(1-hydroxy-1-methylethyl)phenyl)-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidin-6-yl)phenyl)-n'-methoxyurea | HCID 59000902 | 21.2% |
Reaction Steps
The similar reaction as described in Example 40 by using 4-(N-benzyl-N-methylaminomethyl)-2-[N-(2,6-difluorobenzyl)-N-ethoxycarbonylamino]-5-[4-(3-methoxyureido)phenyl]thiophene-3-carboxylic acid (470 mg), diethyl cyanophosphate (167 μl), 4-(1-hydroxy-1-methylethyl)aniline (166 mg) and N-ethyldiisopropylamine (209 μl) gave a crude amide (422 mg). Furthermore, the similar reaction by using ethanol (25.5 ml) and sodium ethoxide (70 mg) gave the title compound (113 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09346822B2 |
| Source dataset | uspto-grants-2016_05 |
| ORD ID | ord-b417f0bab4d34003a5887e6b175f46bd |
| Source note | uspto-grants-2016_05 |