HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-Amino-5-chlorothiazole hydrochloride → N-(5-Chloro-thiazol-2-yl)-3-cyclopentyl-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-oxoisoindolin-2-yl)propanoic acid | HCID 1477119 | — |
| Reactant | (S)-3-cyclohexyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-N-thiazol-2-yl-propionamide | HCID 9947513 | — |
| Product | N-(5-Chloro-thiazol-2-yl)-3-cyclopentyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-propionamide | HCID 10200378 | 74.4% |
Reaction Steps
BOP coupling of 3-Cyclopentyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-propionic acid (prepared in Example 1, Step A; 277 mg; 1.0 mmol) and 2-amino-5-chlorothiazole hydrochloride (397 mg; 2.30 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) 290 mg (74%) of N-(5-Chloro-thiazol-2-yl)-3-cyclopentyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-propionamide as a light yellow solid: EI-HRMS m/e calcd for C19H21N3O2S (M+) 389.0965, found 389.0966.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06482951B2 |
| Source dataset | uspto-grants-2002_11 |
| ORD ID | ord-7f44a336bded4089b0b51b1325ceec09 |
| Source note | uspto-grants-2002_11 |