Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hexane | HCID 8058 | — |
| Reactant | Cyanogen Bromide | HCID 10476 | — |
| Reactant | Sodium Acetate | HCID 517045 | — |
| Reactant | HCID 71008948 | HCID 71008948 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 71008528 | HCID 71008528 | 58.5% |
Reaction Steps
A solution of (R)-3-amino-3-[1-(3-bromo-phenyl)-1H-pyrazol-4-yl]-2,2-difluoro-butan-1-ol (5.1 g, 14.73 mmol) and sodium acetate (3.62 g, 44.2 mmol) in ethanol (90 ml) was warmed to 40° C. Cyanogen bromide (1.71 g, 16.21 mmol) was added and the mixture allowed to stir at 40° C. for 16 hours. Removal of the solvent at reduced pressure followed by purification of the resultant crude material by column chromatography on silica gel using a 3:2-mixture of hexane and ethyl acetate as the eluent yielded the (R)-1-[1-(3-bromo-phenyl)-1H-pyrazol-4-yl]-3-cyanato-2,2-difluoro-1-methyl-propylamine (3.2 g, 58% yield) as a colorless sticky solid. MS (ISP): m/z=369.2 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08785436B2 |
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| Source dataset | uspto-grants-2014_07 |
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| ORD ID | ord-c3b21748bf5247ddbe596fc82fc3f107 |
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| Source note | uspto-grants-2014_07 |
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