Trifluoroacetic acid → HCID 51039081, compound

To a solution of phenyl dichlorophosphate (0.1 ml, 0.625 mmol) in DMF (0.1 ml) at 0° C. under inert atmosphere, was added dropwise a solution of 4-[({[3-(4-methoxyphenyl)-5-phenyl-1H-pyrrol-2-yl]carbonyl}amino)methyl]benzoic acid (0.206 g, 0.5 mmol) in CH2Cl2 (2.5 ml), and the resulting mixture was stirred at room temperature for 10 minutes. 2-(Tritylsulfanyl)aniline (0.404 g, 1.0 mmol) and triethylamine (4.17 ml, 30 mmol) were added subsequently, and the mixture was stirred at room temperature for 16 h. Ethyl acetate (40 ml) was added, and the obtained solution was washed with HCl 0.1N (3×7 ml), water (7 ml), and NaOH 1N (3×7 ml), dried over Na2SO4 and evaporated under reduced pressure. This material was dissolved in CH2Cl2 (5 ml), and cooled to 0° C. Trifluoroacetic acid (0.49 ml, 6.4 mmol) and triethylsilane (0.09 ml, 0.55 mmol) were added subsequently, and the resulting mixture was stirred at room temperature for 2 h. NaHCO3 (7.7 ml, saturated aqueous solution) was added and the resulting mixture was stirred for 30 min. The organic layer was separated and the aqueous layer was extracted with CH2Cl2 (3×15 ml). The combined organic fractions were dried over Na2SO4 and evaporated under reduced pressure, to obtain 0.216 g (0.404 mmol) of 3-(4-methoxyphenyl)-5-phenyl-N-(4-{[(2-sulfanylphenyl)amino]carbonyl}benzyl)-1H-pyrrole-2-carboxamide: Yield 81%; m.p. 134-135° C.; IR 3407, 3384, 3233, 1681, 1638, 1525, 1493, 1249 cm−1; 1H-NMR (300 MHz, δ ppm, CDCl3) 10.22 (s, 1H), 8.93 (s, 1H), 8.48 (dd, J=8.3 Hz, J′=1.0 Hz, 1H), 7.63 (d, J=8.3 Hz, 4H), 7.43-7.35 (m, 6H), 7.34-7.20 (m, 4H), 6.97-6.90 (m, 3H), 6.49 (d, J=3.0 Hz, 1H), 6.24 (t, J=6.0 Hz, 1H), 4.51 (d, J=6.0 Hz, 2H), 3.81 (s, 3H); 13C-NMR (126 MHz, δ ppm, DMSO-d6) 165.4, 161.2, 158.0, 143.5, 135.9, 133.5, 133.0, 132.3, 131.6, 129.9, 128.7, 127.9, 127.8, 127.6, 127.4, 127.1, 126.9, 126.8, 124.6, 123.9, 122.6, 114.0, 113.4, 108.3, 55.0, 42.2.

1. stirringthe mixture was stirred at room temperature for 16 h
2. washthe obtained solution was washed with HCl 0.1N (3×7 ml), water (7 ml), and NaOH 1N (3×7 ml)
3. dry with materialdried over Na2SO4
4. customevaporated under reduced pressure
5. dissolutionThis material was dissolved in CH2Cl2 (5 ml)
6. temperaturecooled to 0° C
7. stirringthe resulting mixture was stirred at room temperature for 2 h
8. stirringthe resulting mixture was stirred for 30 min
9. customThe organic layer was separated
10. extractionthe aqueous layer was extracted with CH2Cl2 (3×15 ml)
11. dry with materialThe combined organic fractions were dried over Na2SO4
12. customevaporated under reduced pressure

ORD record

ord-3d6931f32f414ad5b5afbb34aaa3bdb4

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08685992B2