2-Amino-5-chlorothiazole hydrochloride → HCID 10181609, compound

Participants

Reaction Steps

BOP coupling of (S)-3-cyclohexyl-2-(4-Chloro-1-oxo-1,3-dihydro-isoindol-2-yl)-propionic acid (ca. 1:1 mixture of regioisomers, prepared in Example 36, Step C; 151 mg; 0.47 mmol) and 2-amino-5-chlorothiazole hydrochloride(186 mg; 1.05 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 9, Step B) provided after chromatography (Biotage 40M column, eluent: 5% to 20% gradient of ethyl acetate/hexanes) 67 mg of (S)-N-(5-Chloro-thiazol-2-yl)-3-cyclohexyl-2-(4-Chloro-1-oxo-1,3-dihydro-isoindol-2-yl)-propionamide: EI-HRMS m/e calcd for C20H21Cl2N3O2S (M+) 437.0731, found 437.0727; and 46 mg of regioisomeric S)-N-(5-Chloro-thiazol-2-yl)-3-cyclohexyl-2-(7-Chloro-1-oxo-1,3-dihydro-isoindol-2-yl)-propionamide: EI-HRMS m/e calcd for C20H21Cl2N3O2S (M++Na+) 437.0731, found 437.0726.

Provenance & Evidence