Diisopropylethylamine → ((S)-2-{3-[4-(4-cyano-phenyl)-pyrazol-1-ylmethyl]-benzoylamino}-4,5,6,7-tetrahydro-benzothiazol-6-yl)-carbamic acid tert-butyl ester

Participants

Reaction Steps

Dissolve 3-[4-(4-cyano-phenyl)-pyrazol-1-ylmethyl]-benzoic acid (0.25 g, 0.82 mmol) and ((S)-2-amino-4,5,6,7-tetrahydro-benzothiazol-6-yl)-carbamic acid tert-butyl ester (0.22 g, 0.82 mmol) and TBTU (0.40 g, 1.24 mmol) and N,N-diisopropylethylamine (0.40 ml, 2.47 mmol) into 1.5 mL dry DMF and stir overnight at room temperature under Ar. Pour the reaction into H2O, giving a precipitate. Filter the solid, wash with H2O, and dry. Extract the filtrate 3 times with EtOAc and washed 4 times with H2O, 3 times with aq. NH4Cl and once with aq.Na2CO3. Dry the organic phase and concentrate to give an oil. Both crops are combined and purified via prep plate chromatography eluting with 3% MeOH/CH2Cl2 to give 0.42 g, 92% yield as a clear hard resin of ((S)-2-{3-[4-(4-cyano-phenyl)-pyrazol-1-ylmethyl]-benzoylamino}-4,5,6,7-tetrahydro-benzothiazol-6-yl)-carbamic acid tert-butyl ester.

Provenance & Evidence