HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → HCID 131727599, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| 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 | 2-(3-Fluorophenyl)pyrimidine-5-carboxylic acid | HCID 45073363 | — |
| Reactant | Cis-(3R, 4S)-1-Boc-3-aMino-4-hydroxypyrrolidine | HCID 50986390 | — |
| Solvent | acetonitrile N,N-dimethylformamide | HCID 21891449 | — |
| Product | HCID 131727599 | HCID 131727599 | 140.5% |
Reaction Steps
To a solution of 2-(3-fluorophenyl)pyrimidine-5-carboxylic acid (900 mg, 4.12 mmol) in CH3CN/DMF (10 mL/3 mL) was added HATU (1.73 g, 4.54 mmol), DIPEA (1.44 mL, 0.83 mmol) and cis-tert-butyl 3-amino-4-hydroxypyrrolidine-1-carboxylate (918 mg, 4.54 mmol). After 2 hrs, the solvents were removed in vacuo and the residue purified by chromatography (silica, 100% DCM to 5% MeOH/DCM) to give the desired product, cis-tert-butyl 3-(2-(3-fluorophenyl)pyrimidine-5-carboxamido)-4-hydroxypyrrolidine-1-carboxylate (2.33 g, 80%). LC/MS (M+Na)=425.3 observed, 425.16 expected.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07582643B2 |
| Source dataset | uspto-grants-2009_09 |
| ORD ID | ord-64384a6b055b425bb5ba7a647385e20c |
| Source note | uspto-grants-2009_09 |