Triethylamine → HCID 178440395, compound

Participants

Reaction Conditions

Reaction Steps

(Z)-4-(4-chloroquinolin-2(1H)-ylidene)-3-propyl-1H-pyrazol-5(4H)-one (1.0 g, 3.48 mmol) was stirred in DMF at ambient temperature and Di-t-butyl dicarbonate (2.28 g, 10.5 mmol) was added followed by triethylamine (2.43 mL, 17.4 mmol). After 24 hrs, the reaction mixture was diluted with EtOAc and worked up with DI water. The organic phase was washed with brine and dried over MgSO4, and concentrated to dryness and triturated with methanol. The resulting (Z)-tert-butyl 2-(1-(tert-butoxycarbonyl)-5-oxo-3-propyl-1H-pyrazol-4(5H)-ylidene)-4-chloroquinoline-1 (2H)-carboxylate (0.1 g, 0.21 mmol) was stirred in ethanol and 4-aminothiophenol (0.031 g, 0.25 mmol) was added. The reaction mixture was heated at 30° C. for 2 hrs, concentrated to dryness, and carried out to the next step without further purification. The resulting (Z)-tert-butyl 4-(4-aminophenylthio)-2-(1-(tert-butoxycarbonyl)-5-oxo-3-propyl-1H-pyrazol-4(5H)-ylidene)quinoline-1(2H)-carboxylate was dissolved in pyridine (1-2 mL) and treated with methanesulfonyl chloride (0.048 mL, 0.61 mmol). After 2-4 hr, the solvent was evaporated and the solid redissolved in dichloromethane. Trifluoroacetic acid (1.2 mL) was added dropwise. The final compound was purified by LC-MS to yield Example 26. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.73 (t, J=7.33 Hz, 3H) 1.27-1.37 (m, 2H) 2.30 (t, J=7.33 Hz, 2H) 3.14 (s, 3H) 6.80 (s, 1H) 7.43 (d, J=8.59 Hz, 2H) 7.63 (t, J=7.58 Hz, 1H) 7.72 (d, J=8.59 Hz, 2H) 7.84-7.95 (m, 2H) 8.14 (d, J=8.08 Hz, 1H) 10.34 (s, 1H); ESI-MS: m/z calc'd for C22H22N0O3S2 454.57. found 455.2 (M+H)+.

Provenance & Evidence