Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate | HCID 151348 | — |
| Reactant | HCID 67308714 | HCID 67308714 | — |
| Reactant | HCID 178418300 | HCID 178418300 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 58338347 | HCID 58338347 | 22.5% |
Reaction Steps
108 mg of (1H-benzotriazol-1-yloxy)[tris(dimethylamino)]phosphonium hexafluorophosphate (BOP), 33 mg of hydroxybenzotriazole (HOBT), 17 mg of ammonium chloride and 0.1 ml of diisopropylethylamine are successively added to a solution of 80 mg of 4-[4-(6-cyanopyridin-3-yl)-9H-carbazol-9-yl]-2-[(3-hydroxy-3-methylbutyl)amino]benzoic acid in 10 ml of N,N-dimethylformamide. The reaction mixture is stirred at ambient temperature for 12 hours and then diluted with distilled water and extracted with ethyl acetate. The organic phase is subsequently washed with distilled water and a saturated solution of sodium chloride, dried over magnesium sulphate, filtered and concentrated under reduced pressure. The residue is purified by silica gel chromatography, elution being carried out with a mixture of dichloromethane and methanol (96/4 by volume), so as to give 18 mg of 4-[4-(6-cyanopyridin-3-yl)-9H-carbazol-9-yl]-2-[(3-hydroxy-3-methylbutyl)amino]benzamide in the form of a white solid, the characteristics of which are the following:
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08309721B2 |
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| Source dataset | uspto-grants-2012_11 |
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| ORD ID | ord-7159da633e964c418b9266374817489b |
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| Source note | uspto-grants-2012_11 |
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