58077-68-2, 4-(4-Methylpiperazin-1-yl)butanoic acid is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated
58077-68-2, A solution of (1R,2R)-2-[[trans-2-[(1E,3E)-4-(4-cyano-2-fluorophenyl)-1,3-butadienyl]-1,3-dioxan-5-yl]thio]-1-(2,4-difluorophenyl)-1-[(1H-1,2,4-triazol-1-yl)methyl]propyl 2-(hydroxymethyl)benzoate (1.07 g, 1.58 mmol) obtained from Example 17-(4) in dichloromethane (20 ml) was cooled to 0C, and 4-(N,N-dimethylamino)pyridine (386.1 mg, 3.16 mmol), 4-(4-methyl-1-piperazinyl)butanoic acid (described in J. Med. Chem., 43, 1493 (2000); 529.5 mg, 2.84 mmol), and 1-ethyl-3-[3-(N,N-dimethylamino)propyl]carbodiimide (666.8 mg, 3.48 mmol) were added thereto. The reaction solution was stirred at room temperature for 2 hours, diluted with dichloromethane, and then the organic layer was washed successively with water and a saturated aqueous solution of sodium chloride. The solvent was evaporated under reduced pressure, and the residue was subjected to chromatography on a silica gel (50 g) column (eluent; ethyl acetate : methanol = 4 : 1) to give a mixture of the title target compound and 4-(N,N-dimethylamino)pyridine. The mixture was purified by recycle preparative HPLC [LC-908; Japan Analytical Industry Co., Ltd.; GPC column JAIGEL-1H (20 mm i.d. x 600 mm) and JAIGEL-2H (20 mm i.d. x 600 mm) connected in series for use; solvent, chloroform] to afford the title target compound (901.1 mg, 67% yield) as a colorless amorphous solid. NMR spectrum (400 MHz, CDCl3) delta ppm: 1.46 (3H, dd, J=7, 2 Hz), 1.85 (2H, quint., J=7 Hz), 2.27 (3H, s), 2.3-2.6 (8H, br), 2.37 (2H, t, J=7 Hz), 2.45 (2H, t, J=7 Hz), 3.05 (1H, tt, J=11, 5 Hz), 3.51 (1H, t, J=11 Hz), 3.53 (1H, t, J=11 Hz), 4.01 (1H, q, J=7 Hz), 4.10-4.20 (2H, m), 4.99 (1H, d, J=4 Hz), 5.30-5.56 (4H, m), 5.85 (1H, dd, J=15, 4 Hz), 6.57 (1H, dd, J=15, 10 Hz), 6.73 (1H, d, J=15 Hz), 6.88-7.00 (3H, m), 7.34 (1H, dd, J=10, 1 Hz), 7.37-7.46 (3H, m), 7.52-7.60 (3H, m), 7.79 (1H, d, J=8 Hz), 7.90 (1H, s), 7.95 (1H, s) IR spectrum nu max KBr cm-1: 2230, 1729, 1503, 1357, 1257, 1139, 1051, 973 Mass spectrum m/z (ESI): 845 (M++1) Specific rotation [alpha]D25 -1.8 (c=1.06, CHCl3). A solution of (1R,2R)-2-[[trans-2-[(1E, 3E)-4-(4-cyano-2-fluorophenyl)-1,3-butadienyl]-1,3-dioxan-5-yl]thio]-1-(2,4-difluorophenyl)-1-[(1H-1,2,4-triazol-1-yl)methyl]propyl] 2-[[4-(4-methyl-1-piperazinyl)butyryl]oxymethyl]benzoate (290.5 mg, 0.34 mmol) obtained above in ethyl acetate (5 ml) was cooled to 0C, and hydrogen chloride (4N ethyl acetate solution; 86 mul, 0.35 mmol) was added thereto, and then the mixture was stirred at 0C for 5 minutes. The solvent was distilled off under reduced pressure to afford the mono hydrochloric acid salt of the title compound (305.1 mg, quantitative yield) as a pale yellow amorphous solid. NMR spectrum (400 MHz, CDCl3) delta ppm: 1.46 (3H, dd, J=7, 2 Hz), 1.90 (2H, br), 2.47 (2H, t, J=7 Hz), 2.6-2.8 (13H, br d), 3.05 (1H, tt, J=11, 5 Hz), 3.51 (1H, t, J=11 Hz), 3.53 (1H, t, J=11 Hz), 4.01 (1H, q, J=7 Hz), 4.10-4.15 (1H, m), 4.18 (1H, ddd, J=11, 5, 2 Hz), 4.99 (1H, d, J=4 Hz), 5.44 (1H, d, J=14 Hz), 5.46-5.53 (2H, m), 5.55 (1H, d, J=15 Hz), 5.85 (1H, dd, J=15, 4 Hz), 6.57 (1H, dd, J=15, 11 Hz), 6.74 (1H, d, J=15 Hz), 6.89-6.93 (2H, m), 6.94 (1H, dd, J=15, 11 Hz), 7.34 (1H, dd, J=10, 1 Hz), 7.40-7.47 (3H, m), 7.54-7.62 (3H, m), 7.84 (1H, d, J=7 Hz), 7.89 (1H, s), 7.97 (1H, s) IR spectrum nu max KBr cm-1: 2230, 1729, 1503, 1274, 1256, 1139, 1051, 973 Mass spectrum m/z (ESI): 845 [M(free base)++1] Specific rotation [alpha]D25 -4.5 (c=0.89, CHCl3)
The synthetic route of 58077-68-2 has been constantly updated, and we look forward to future research findings.
Reference£º
Patent; Sankyo Company, Limited; EP1362856; (2003); A1;,
Piperazine – Wikipedia
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