Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methylamine | HCID 6329 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate | HCID 2733207 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | 1-(5-Bromopyridin-2-YL)cyclopropanecarboxylic acid | HCID 69476153 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 67998436 | HCID 67998436 | — |
Reaction Steps
2-(1H-Benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (0.13 g; alternatively, 2-(7-aza-1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate may be used) was added to a solution of 1-(5-bromo-pyridin-2-yl)-cyclopropanecarboxylic acid (0.10 g) and ethyl-diisopropyl-amine (70 μL) in N,N-dimethylformamide (1 mL) at room temperature. The solution was stirred for 20 min prior to the addition of methylamine (2 mol/L in tetrahydrofuran, 0.62 mL). The resulting solution was stirred at room temperature for 1 h and then concentrated. The residue was purified by HPLC on reversed phase (0.125% aqueous ammonia/methanol) to afford the title compound. Yield: 0.10 g (95% of theory); LC (method 1): tR=1.44 min; Mass spectrum (ESI+): m/z=255/257 (Br) [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08933072B2 |
|---|
| Source dataset | uspto-grants-2015_01 |
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| ORD ID | ord-8db6d47ed5164dd8b0ac551ed82e784b |
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| Source note | uspto-grants-2015_01 |
|---|
