Methanol → HCID 178502412, compound

Participants

Reaction Steps

HATU (66 mg, 0.17 mmol) was added to a stirred solution of a TFA salt of 2,2′-bis(2-((2S)-2-pyrrolidinyl)-1H-imidazol-5-yl)-5,5′-bi-1,3-thiazole (40 mg, 0.045 mmol), (S)-2-(methoxycarbonylamino)-3-methylbutanoic acid (31 mg, 0.18 mmol) and DIEA (0.078 mL, 0.45 mmol) in dimethylformamide (2 mL) at room temperature. The reaction was stirred for 3 h, diluted with methanol (2 mL) and water (2 mL) and stirred for 15 min. The reaction mixture was concentrated to dryness in vacuo and purified by preparative HPLC (Waters Sunfire C18 column 30×150 mm 5 u, eluted with a gradient of 10 to 80% acetonitrile/water/0.1% TFA) to yield a trifluoroacetate salt of methyl ((1S)-1-(((2S)-2-(4-(2′-(2-((2S)-1-((2S)-2-((methoxycarbonyl)amino)-3-methylbutanoyl)-2-pyrrolidinyl)-1H-imidazol-4-yl)-5,5′-bi-1,3-thiazol-2-yl)-1H-imidazol-2-yl)-1-pyrrolidinyl)carbonyl)-2-methylpropyl)carbamate (23 mg, 0.023 mmol, 52% yield) as a yellow solid.

Provenance & Evidence