Compound 6

HHS-483

From: Global targeting of functional tyrosines using sulfur-triazole exchange chemistry

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InChIKey SJMDCKZISXSWGD-UHFFFAOYSA-N

Synonyms:
  • 4-((3-(4-fluorophenyl)-1H-1,2,4-triazol-1-yl)sulfonyl)-N-(prop-2-yn-1-yl)benzamide

Compound data: 1H NMR

Compound data: 13C NMR

Compound data: 19F NMR

Compound data: HPLC

Compound data: Crystallographic data

Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.

To a solution of compound 1 (0.1 g, 0.39 mmol, 1.0 eq.) in anhydrous DCM (1.9 mL, 0.2 M) was added the corresponding triazole (0.47 mmol, 1.2 eq.) and DIPEA (124 µL, 0.47 mmol, 1.2 eq.) at 0 oC. Then the reaction mixture was stirred at room temperature for overnight. The crude product was directly loaded and purified using silica gel flash column chromatography (acetone/DCM = 3:100 to 7:100) to afford HHS-483. Yield: 77%, 1H NMR (600 MHz, (CD3)2CO) δ 9.19 (s, 1H), 8.40 (s, 1H), 8.31 – 8.26 (m, 2H), 8.21 – 8.17 (m, 2H), 8.14 – 8.09 (m, 2H), 7.29 – 7.23 (m, 2H), 4.20 (dd, J = 5.5, 2.6 Hz, 2H), 2.69 (t, J = 2.6 Hz, 1H). 13C NMR (150 MHz, (CD3)2CO) δ 165.84, 165.33, 164.92, 164.19, 147.85, 141.62, 139.13, 129.95 (d, J = 8.7 Hz), 129.66 (d, J = 5.7 Hz), 126.63 (d, J = 3.0 Hz), 116.63 (d, J = 22.1 Hz), 80.75, 72.36, 29.75. 19F NMR (564 MHz, (CD3)2CO) δ -111.48. ESI-TOF (HRMS) m/z [M+H]+ calculated for C18H14FN4O3S 385.0765, found 385.0755.

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