Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Pyrrolidine | HCID 31268 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| 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 | Ethanedioic acid, 1-[2-(4-iodo-2-pyridinyl)hydrazide] | HCID 68712583 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 68715634 | HCID 68715634 | 34.4% |
Reaction Steps
To a solution of [2-(4-iodopyridin-2-yl)hydrazino](oxo)acetic acid (0.64 g, 2.10 mmol) in di-methylformamide (21 mL) was added diisopropylethylamine (1.65 mL, 9.47 mmol), pyrrolidine (0.74 mL, 8.84 mmol) and finally HATU (2.40 g, 6.31 mmol). The resulting mixture was stirred at room temperature under argon atmosphere for 18 hours. The solvent was removed under reduced pressure, water was added and it was extracted with ethyl acetate. The combined organic layers were washed with brine, dried and concentrated. The crude was purified by reverse phase chromatography on a silica C18 cartridge eluting with water/acetonitrile:methanol (1:1), using a gradient from 100% water to 100% acetonitrile:methanol (1:1), to yield the title compound (0.26 g, 30%) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08258122B2 |
|---|
| Source dataset | uspto-grants-2012_09 |
|---|
| ORD ID | ord-d264cf19f88f43cc8bd570fcfec8c46f |
|---|
| Source note | uspto-grants-2012_09 |
|---|
