HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylcarbodiimide → 2(S)-{4-[3-(5-Chloro-2-hydroxy-phenyl)-1-(2-hydroxy-ethyl)-1H-pyrazol-4-ylethynyl]-phenylcarbamoyl}-piperidine-1-carboxylic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylcarbodiimide | HCID 12734 | — |
| Reactant | (2R)-1-[(tert-butoxy)carbonyl]piperidine-2-carboxylic acid | HCID 688618 | — |
| Reactant | 2-[4-(4-Amino-phenylethynyl)-1-(2-hydroxy-ethyl)-1H-pyrazol-3-yl]-4-chloro-phenol | HCID 135974913 | — |
| Reactant | HCID 135974981 | HCID 135974981 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 2(S)-{4-[3-(5-Chloro-2-hydroxy-phenyl)-1-(2-hydroxy-ethyl)-1H-pyrazol-4-ylethynyl]-phenylcarbamoyl}-piperidine-1-carboxylic acid tert-butyl ester | HCID 135974931 | 95.2% |
Reaction Steps
Using the same procedure for the preparation of compound 4A, reaction of compound 2A (2.17 g, 6.13 mmol) and N-Boc-2(S)-piperidinecarboxylic acid (3A) (5.63 g, 24.55 mmol) in the presence of DMAP (0.30 g, 2.46 mmol) and (DIPC, 3.80 mL, 24.54 mmol) in anhydrous THF (40 mL) provided the title compound (9A, 3.30 g) as a foam-like powder in 95.2% yield. The 1H NMR and LCMS data are exactly same with those of compound 4A.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07923004B2 |
| Source dataset | uspto-grants-2011_04 |
| ORD ID | ord-c10014ff579c41e2aeee973a0d47dd8e |
| Source note | uspto-grants-2011_04 |