Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | N-bromobutanimide | HCID 67184 | — |
| Reactant | HCID 46917346 | HCID 46917346 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 46917419 | HCID 46917419 | — |
Reaction Steps
A solution of 5-{2-[4-(2,6-diethyl-phenylcarbamoyl)-2-methyl-phenylamino]-pyrimidin-4-yl}-1-methyl-1H-pyrrole-3-carboxylic acid (2,6-diethyl-phenyl)-amide (100 mg, 0.1626 mmol) and NBS (29 mg, 0.1626 mmol) in 7.5 mL of DMF was stirred at room temperature for 1 h. The mixture was then diluted with AcOEt and washed with water. The organic layer was dried over Na2SO4 and the solvent removed under reduced pressure. The target product was purified by preparative HPLC (39.8 mg, 35%, Exact Mass: calculated 693.2547, found 693.2548) as well as 2-bromo-5-{2-[4-(2,6-diethyl-phenylcarbamoyl)-2-methyl-phenylamino]-pyrimidin-4-yl}-1-methyl-1H-pyrrole-3-carboxylic acid (2,6-diethyl-phenyl)-amide (24.7 mg, 22%, Exact Mass: calculated 693.2547, found 693.2556.) and 2-bromo-5-{5-bromo-2-[4-(2,6-diethyl-phenylcarbamoyl)-2-methyl-phenylamino]-pyrimidin-4-yl}-1-methyl-1H-pyrrole-3-carboxylic acid (2,6-diethyl-phenyl)-amide (8.1 mg, 6.5%, Exact Mass: calculated 771.1652, found 771.1653).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08772280B2 |
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| Source dataset | uspto-grants-2014_07 |
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| ORD ID | ord-e40859dd6daa4e8084156e1a2a97ba83 |
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| Source note | uspto-grants-2014_07 |
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