Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 2-Aminothiazole | HCID 2155 | — |
| Reactant | Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate | HCID 151348 | — |
| Reactant | (S)-3-cyclohexyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-N-thiazol-2-yl-propionamide | HCID 9947513 | — |
| Reactant | HCID 69696537 | HCID 69696537 | — |
| Product | HCID 18402181 | HCID 18402181 | 34.7% |
Reaction Steps
BOP coupling of (S)-3-cyclohexyl-2-(5-nitro-1-oxo-1,3-dihydro-isoindol-2-yl)-propionic acid (ca. 1:1 mixture of regioisomers, prepared in Step C; 301 mg; 0.91 mmol) and 2-aminothiazole (116 mg; 1.12 mol) in a manner similar to that used for the preparation of (S)-3-cyclohexyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-N-thiazol-2-yl-propionamide (as outlined in Example 1, Step B) provided after chromatography (Biotage 40M, eluent: 30% ethyl acetate/hexanes) 131 mg of 3-Cyclohexyl-2-(5-nitro-1-oxo-1,3-dihydro-isoindol-2-yl)-N-thiazol-2-yl-propionamide: EI-HRMS m/e calcd for C20H22N4O4S (M+) 414.1362, found 414.1362 and 121 mg of regioisomeric 3-Cyclohexyl-2-(6-nitro-1-oxo-1,3-dihydro-isoindol-2-yl)-N-thiazol-2-yl-propionamide: EI-HRMS m/e calcd for C20H22N4O4S (M+) 414.1362, found 414.1368.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06482951B2 |
|---|
| Source dataset | uspto-grants-2002_11 |
|---|
| ORD ID | ord-f94321ad988248608f8acbc8c738d816 |
|---|
| Source note | uspto-grants-2002_11 |
|---|
