HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanol → Pyrrolidine-1-carboxylic acid {4-[3-chloro-4-(3-phenylacetylureido)phenoxy]pyridin-2-yl}amide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | Phenylacetyl isocyanate | HCID 12259960 | — |
| Reactant | 4-(4-Amino-3-chlorophenoxy)-2-[(pyrrolidin-1-yl)carbonylamino]pyridine | HCID 23153533 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | Pyrrolidine-1-carboxylic acid {6-[2-fluoro-4-(3-phenylacetylthioureido)phenoxy]pyrimidin-4-yl}amide | HCID 11248939 | — |
| Product | Pyrrolidine-1-carboxylic acid {4-[3-chloro-4-(3-phenylacetylureido)phenoxy]pyridin-2-yl}amide | HCID 57677481 | 34% |
Reaction Steps
Pyrrolidine-1-carboxylic acid [4-(4-amino-3-chlorophenoxy)pyridin-2-yl]amide (20 mg) was dissolved in N,N-dimethylformamide (1.0 ml), and then a solution of phenylacetyl isocyanate in hexane (0.019 ml, Production Example 1) was added thereto, followed by stirring at room temperature for 1 hr. To the reaction mixture was added ethyl acetate and water to partition. The organic layer was washed with brine, and dried over anhydrous sodium sulfate. The solvent was evaporated to give a residue, which was then suspended in ethyl acetate:methanol=1:1. The solid was filtered off, washed with methanol, and dried under aeration to provide the titled compound (10 mg, 34%) as pale yellow powder.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07531532B2 |
| Source dataset | uspto-grants-2009_05 |
| ORD ID | ord-89c7c6fe517b4c579bf15705ba2f676f |
| Source note | uspto-grants-2009_05 |