HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-Aminothiazole → (S)-3-Cyclohexyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-N-pyrazin-2-yl-propionamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-Aminothiazole | HCID 2155 | — |
| Reactant | Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate | HCID 151348 | — |
| Reactant | (R)-3-cyclohexyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-N-thiazol-2-yl-propionamide | HCID 10133709 | — |
| Reactant | 3-Cyclopentyl-2-(1-oxoisoindolin-2-yl)propanoic acid | HCID 18402209 | — |
| Product | (S)-3-Cyclohexyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-N-pyrazin-2-yl-propionamide | HCID 10109378 | — |
Reaction Steps
BOP coupling of (3-Cyclopentyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-propionic acid (prepared in Step A; 273 mg; 1.00 mmol) and 2-aminothiazole (100 mg; 1.00 mmol) in a manner similar to that used for the preparation of (R)-3-cyclohexyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-N-thiazol-2-yl-propionamide (outlined in Example 9, Step B) provided after flash chromatography (Merck Silica gel 60, 230-400 mesh, eluent: 40% ethyl acetate/hexanes) 132 mg (37%) of 3-Cyclopentyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-N-thiazol-2-yl-propionamide as a white solid: ES-HRMS m/e calcd for C19H21N3O2SNa (M++Na+) 378.1247, found 378.1250.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06482951B2 |
| Source dataset | uspto-grants-2002_11 |
| ORD ID | ord-57d84659329043d5bd67e12568d2782d |
| Source note | uspto-grants-2002_11 |