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Methyl 1-amino-3-phenyl-1H-pyrrole-2-carboxylate (0.400 g, 1.85 mmol) and 2-(N-(tert-butyl)sulfamoyl)thiazole-4-carboxylic acid (0.733 g, 2.77 mmol) (Johnson et al., WO 2011/28741) were dissolved in DMF (10 mL) and cooled to 0° C. HATU (1.41 g, 3.70 mmol) was added slowly, followed by DIPEA (1.29 mL, 7.40 mmol). The reaction mixture was allowed to reach ambient temperature over 14 h and was diluted with water (25 mL) and extracted with ethylacetate (3×20 mL). The organic layer was separated and the combined organic portions dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography using CombiFlash (REDISEP®, silica gel, 40 g, 38% EtOAc/hexanes) to afford methyl 1-(2-(N-(tert-butyl)sulfamoyl)thiazole-5-carboxamido)-3-phenyl-1H-pyrrole-2-carboxylate (0.250 g, 29.2%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.26 (s, 9H), 3.50 (s, 3H), 6.31 (d, J=3.2 Hz, 1H), 7.25-7.43 (m, 6H), 8.39 (s, 1H), 8.77 (s, 1H), 11.83 (s, 1H).

1. extractionextracted with ethylacetate (3×20 mL)
2. customThe organic layer was separated
3. dry with materialthe combined organic portions dried over anhydrous sodium sulfate
4. filtrationfiltered
5. concentrationconcentrated under reduced pressure
6. customThe residue was purified by column chromatography