Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Methyl bromoacetate | HCID 60984 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | HCID 71293568 | HCID 71293568 | — |
| Product | HCID 71293538 | HCID 71293538 | — |
Reaction Steps
To a stirred suspension of N-(2-aminoethyl)-5-{4-[3-fluoro-4-({[(2-fluoro-5-methylphenyl)amino]carbonyl}amino)phenoxy]pyridin-2-yl}-1H-pyrrole-3-carboxamide (120 mg, 0.24 mmol) in 10 ml of anhydrous THF were added N,N-diisopropylethylamine (1 ml, 5.6 mmol) and methyl bromoacetate (300 mg, 2.0 mmol). The mixture was heated at 55° C. for 2 hours and poured into 100 ml of water with vigorous stirring. The precipitates were filtered and dried in vacuo to give the crude, which was purified by silica gel chromatography eluting with 3˜4% of MeOH in CHCl3 to afford dimethyl 2,2′-[(2-{[(5-{4-[3-fluoro-4-({[(2-fluoro-5-methylphenyl)amino]carbonyl}amino)phenoxy]pyridin-2-yl}-1H-pyrrol-3-yl)carbonyl]amino}ethyl)imino]diacetate as white solid. Yield: 110 mg, 71%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08906944B2 |
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| Source dataset | uspto-grants-2014_12 |
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| ORD ID | ord-9cae68bfd5014f228a4ecf49fe963105 |
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| Source note | uspto-grants-2014_12 |
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