HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-Amino-5-chlorothiazole hydrochloride → N-(5-Chloro-thiazol-2-yl)-3-cycloheptyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-propionamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-Amino-5-chlorothiazole hydrochloride | HCID 148743 | — |
| 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 | 3-Cycloheptyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-propionic acid | HCID 18402168 | — |
| Product | N-(5-Chloro-thiazol-2-yl)-3-cycloheptyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-propionamide | HCID 10273487 | 40.1% |
Reaction Steps
BOP coupling of 3-Cycloheptyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-propionic acid (prepared in Step E; 177 mg; 0.59 mmol) and 2-amino-5-chlorothiazole hydrochloride (168 mg; 0.95 mmol) 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 flash chromatography (Biotage 40M, eluent: 20% ethyl acetate/hexanes) 99 mg (40%) of N-(5-Chloro-thiazol-2-yl)-3-cycloheptyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-propionamide as an off white foam EI-HRMS m/e calcd for C21H24ClN3O2S (M+) 417.1278, found 417.1289.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06482951B2 |
| Source dataset | uspto-grants-2002_11 |
| ORD ID | ord-d2812026a1f041398ab19992e6ff7421 |
| Source note | uspto-grants-2002_11 |