1,2-Dichloro-3-isocyanatobenzene → HCID 67271728, compound

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Reaction Steps

Using the same general approach as for Example 524, ethyl 2-(3-(5-amino-3-(thiophen-3-yl)-1H-pyrazol-1-yl)phenyl)acetate (0.2258 g, 0.450 mmol, 1.00 eq) was transformed to ethyl 2-(3-(5-amino-3-(thiophen-3-yl)-1H-pyrazol-1-yl)phenyl)propanoate. This, in turn, was combined with 2,3-dichlorophenyl isocyanate, according to general method A, to afford 2-(3-(5-(3-(2,3-dichlorophenyl)ureido)-3-(thiophen-3-yl)-1H-pyrazol-1-yl)phenyl)propanoic acid. Using general method J, this product was combined with 0.5M NH3 in dioxane (4.50 ml, 2.25 mmol, 5.00 eq). to afford 0.1731 g (77%) of pure 1-(1-(3-(1-amino-1-oxopropan-2-yl)phenyl)-3-(thiophen-3-yl)-1H-pyrazol-5-yl)-3-(2,3-dichlorophenyl)urea. 1H NMR (DMSO-d6): δ 9.38 (s, 1H), 8.82 (s, 1H), 8.12-8.09 (m, 1H), 7.88-7.87 (m, 1H), 7.62-7.60 (m, 1H), 7.57-7.42 (m, 6H), 7.36-7.31 (m, 2H), 6.89 (brs, 1H), 6.86 (s, 1H), 3.69 (q, 1H, J=7.2 Hz), 1.36 (d, 3H, J=7.2 Hz); MS (ESI) m/z: 500.0 (M+H+), 502.0 (M+2+H+).

Provenance & Evidence