반응 #535244

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5-fluoro-2-methylbenzoic acid

HATU

DIEA

3-butyl-2,5-dimethyl-1,3,4-thiadiazol-3-ium iodide

→

title compound

(2Z)-2-(3-butyl-5-methyl-1,3,4-thiadiazol-2(3H)-ylidene)-1-(5-fluoro-2-methylphenyl)ethanone

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후처리

1. 1
   농축concentrated in vacuo
2. 2
   기타purified by reverse phase HPLC

실험 절차

In a 20 mL vial 5-fluoro-2-methylbenzoic acid (0.9 mL of 0.2 M in DMA, 1.10 equiv) was added followed by the addition of HATU (76 mg in 0.7 mL of DMA, 0.2 mmol, 1.20 equiv.), DIEA (51 mg in 0.7 mL of DMA, 0.4 mmol, 2.40 equiv.), and finally 3-butyl-2,5-dimethyl-1,3,4-thiadiazol-3-ium iodide (49 mg in 0.7 mL of DMA, 0.17 mmol, 1 equiv.). The mixture was shaken overnight at room temperature and then concentrated in vacuo. The resulting residue was taken up in 1:1 DMSO/MeOH and purified by reverse phase HPLC using a method analogous to that described in Example 53 to provide the title compound. 1H NMR (500 MHz, DMSO-d6/D2O) δ ppm 0.90 (t, 3 H) 1.68-1.76 (m, 2 H) 2.34 (s, 3 H) 2.48 (s, 3 H) 4.16 (t, 2 H) 6.26 (s, 1 H) 7.10-7.16 (m, 1 H) 7.23-7.32 (m, 2 H); MS (ESI) m/z 307 (M+H)+.

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