To a solution of 6-(pyridin-2-yl)hexanoic acid (19d , 1.09 g, 5.64 mmol) in DMF (10 mL) was added HOBt (914 mg, 6.77 mmol), EDCI (1.62 g, 8.46 mmol) and DIEA (2.19 g, 16.9 mmol, 2.95 mL), 4-aminocyclohexan-1-ol (940 mg, 6.20 mmol, 1.10 eq, HCl) was added to the mixture, stirred at 25 °C for 16 h, the residue was purified by Reverse Phase HPLC (column: Waters Xbridge C18 150*50 mm*10 μm; mobile phase: [water (10 mM NH4HCO3)-ACN]; B%: 7%−37%, 10 min) to obtain 19 (106.1 mg, 355 μmol, 6.30% yield) as an off-white solid. HPLC: Rt: 1.78 min, purity: 97.2%. LCMS: Rt: 0.752 min, m/z = 291.0 (M+H)+. 1H NMR: 400 MHz MeOD, δ 8.42 (d, J = 4.00 Hz, 1H), 7.77 – 7.73 (m, 1H), 7.31 – 7.30 (m, 1H), 7.25 – 7.23 (m, 1H), 3.61 – 3.48 (m, 2H), 2.80 – 2.76 (m, 2H), 2.16 – 2.12 (m, 2H), 1.91 – 1.91 (m, 2H), 1.72 – 1.70 (m, 2H), 1.65 – 1.63 (m, 2H), 1.61 – 1.61 (m, 2H), 1.37 – 1.33 (m, 4H), 1.32 – 1.26 (m, 2H). 13C NMR: 400 MHz MeOD. δ 175.538, 163.333, 149.597, 138.868, 124.829, 122.881, 70.591, 38.666, 37.133, 34.973, 31.671, 30.954, 29.861, 27.016.
Xbridge c18 150
Manufactured by Waters Corporation
The Xbridge C18 150 is a high-performance liquid chromatography (HPLC) column manufactured by Waters Corporation. The column is designed for the separation and analysis of a wide range of compounds. The core function of the Xbridge C18 150 is to provide efficient and reliable chromatographic separation.
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Lab products found in correlation
8 protocols using xbridge c18 150
1
Synthesis of 4-Aminocyclohexanol-Coupled Pyridine Derivative
2
Synthesis of N-(1-(azetidin-3-yl)ethyl)-5-(4-(trifluoromethyl)phenoxy)-2-naphthamide
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Example 100
To a solution of (S)—N-(1-(azetidin-3-yl)ethyl)-5-(4-(trifluoromethyl)phenoxy)-2-naphthamide (75 mg, 0.18 mmol, 1 eq) in MeCN (3 mL) was added K2CO3 (62.5 mg, 0.45 mmol, 2.5 eq) and 2-bromo-1,1-difluoroethane (39.4 mg, 0.27 mmol, 2.6 uL, 1.5 eq). The mixture was stirred at 70° C. for 16 hr. The reaction mixture was diluted with H2O (30 mL) and stirred for 5 min. The aqueous phase was extracted with EA (15 mL*3). The combined organic phase was washed with brine (20 mL), dried with anhydrous Na2SO4, filtered and concentrated in vacuum. The residue was purified by prep-HPLC (column: Waters Xbridge C18 150*50 mm*10 um; mobile phase: [water (0.04% NH3H2O)-ACN]; B %: 51%-81%, 11 min) to afford the title compound (26.8 mg, 54.9 umol, 30.33% yield) as a white solid. LCMS (ESI): RT=0.796 min, mass calcd for C25H23F5N2O2 478.17, m/z found 479.3 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ 8.51 (s, 1H), 8.44 (d, J=8.3 Hz, 1H), 8.02-7.90 (m, 3H), 7.74 (d, J=8.8 Hz, 2H), 7.63 (t, J=7.9 Hz, 1H), 7.32 (d, J=7.0 Hz, 1H), 7.15 (d, J=8.5 Hz, 2H), 6.09-5.75 (m, 1H), 4.32-4.19 (m, 1H), 3.34 (t, J=6.8 Hz, 2H), 3.11-2.95 (m, 2H), 2.76 (m, 2H), 2.63-2.52 (m, 2H), 1.09 (d, J=6.5 Hz, 3H).
3
Synthesis and Characterization of 23
4
Synthesis and Purification of Compound 141
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Example 129
To a solution of 129-1 in DCM (1 mL) at 30° C. was added TFA (154.0 mg, 1.4 mmol, 0.1 mL, 12.2 eq). The mixture was stirred at 30° C. for 1 h. The reaction mixture was concentrated under reduced pressure to give a residue, which was basified with NH3·H2O to pH=9 and concentrated under reduced pressure to give a residue, which was purified by prep-HPLC (column: Waters Xbridge C18 150*50 mm*10 um; mobile phase: [water (0.04% NH3H2O+10 mM NH4HCO3)-ACN]; B %: 33%-63%, 11 min) to give Compound 141 (14.9 mg, 35 umol, 32.0% yield) as a white solid. LCMS (ESI): RT=0.825 min, mass calc. for C22H20F3N3O2 415.15, m/z found 416.2 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ 9.25 (d, J=2.0 Hz, 1H), 8.93 (d, J=1.9 Hz, 1H), 8.48 (brd, J=8.8 Hz, 1H), 8.18 (d, J=7.8 Hz, 1H), 7.95-7.89 (m, 2H), 7.87 (d, J=8.6 Hz, 4H), 7.82-7.78 (m, 1H), 5.59 (brs, 1H), 4.49-4.40 (m, 1H), 3.44 (brs, 2H), 3.32 (brs, 2H), 1.16 (d, J=6.8 Hz, 3H).
5
Synthesis of Fluorinated Naphthamide Derivative
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Example 94
To a solution of (R)—N-(1-(azetidin-3-yl)ethyl)-5-(4-(trifluoromethyl)phenoxy)-2-naphthamide (50 mg, 0.12 mmol, 1 eq), KI (2.0 mg, 12.1 umol, 0.1 eq) and K2CO3 (50.0 mg, 0.36 mmol, 3 eq) in ACN (2 mL) at 30° C. was added 2-bromo-1,1-difluoroethane (26.2 mg, 0.18 mmol, 1.5 eq), and the mixture was stirred at 70° C. for 16 h. The reaction mixture was filtered to remove the solid and the filtrate was concentrated under reduced pressure to give a residue. The residue was purified by prep-HPLC (column: Waters Xbridge C18 150*50 mm*10 um; mobile phase: [water (0.04% NH3H2O)-ACN]; B %: 52%-82%, 11 min) to give the title compound (19.9 mg, 41.2 umol, 34.1% yield) as a white solid. LCMS (ESI): RT=0.801 min, mass calc. for C25H23F5N2O2 478.17, m/z found 479.0 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ 8.51 (s, 1H), 8.44 (d, J=8.3 Hz, 1H), 8.02-7.91 (m, 3H), 7.74 (d, J=8.8 Hz, 2H), 7.63 (t, J=7.9 Hz, 1H), 7.32 (d, J=7.5 Hz, 1H), 7.15 (d, J=8.6 Hz, 2H), 6.10-5.76 (m, 1H), 4.32-4.20 (m, 1H), 3.35 (br d, J=3.6 Hz, 2H), 3.06 (t, J=6.8 Hz, 1H), 2.98 (t, J=6.8 Hz, 1H), 2.76 (dt, J=4.2, 16.2 Hz, 2H), 2.62-2.55 (m, 1H), 1.09 (d, J=6.6 Hz, 3H).
6
Synthesis of Fluorinated Quinoline Derivative
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Example 127
To a solution of 127-1 (60 mg, 0.15 mmol, 1 eq) in MeCN (3 mL) was added K2CO3 (52.0 mg, 0.38 mmol, 2.5 eq) and 1-bromo-2-fluoro-ethane (28.68 mg, 0.23 mmol, 1.5 eq). The mixture was stirred at 70° C. for 16 hr. The reaction mixture was diluted with H2O (30 mL) and stirred for 5 min. The aqueous phase was extracted with EA (15 mL*3). The combined organic phase was washed with brine (20 mL), dried with anhydrous Na2SO4, filtered and concentrated in vacuum. The residue was purified by prep-HPLC (column: Waters Xbridge C18 150*50 mm*10 um; mobile phase: [water (0.04% NH3H2O)-ACN]; B %: 48%-78%, 11 min) to afford Compound 139 (11.2 mg, 24.7 umol, 16.4% yield) as a yellow solid. LCMS (ESI): RT=0.788 min, mass calcd for C25H24F4N2O 444.18, m/z found 445.3 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ 8.53 (d, J=1.1 Hz, 1H), 8.46 (d, J=8.3 Hz, 1H), 8.12 (d, J=8.3 Hz, 1H), 7.96-7.88 (m, 3H), 7.81 (d, J=8.9 Hz, 1H), 7.76-7.66 (m, 3H), 7.58 (d, J=6.4 Hz, 1H), 4.43 (t, J=4.8 Hz, 1H), 4.36-4.21 (m, 2H), 3.35-3.27 (m, 2H), 2.99 (t, J=6.6 Hz, 1H), 2.90 (t, J=6.8 Hz, 1H), 2.66 (t, J=4.8 Hz, 1H), 2.62-2.53 (m, 2H), 1.11 (d, J=6.6 Hz, 3H).
7
Synthesis of N-(1-(azetidin-3-yl)ethyl)-5-(4-(trifluoromethyl)phenoxy)-2-naphthamide
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Example 100
To a solution of (S)—N-(1-(azetidin-3-yl)ethyl)-5-(4-(trifluoromethyl)phenoxy)-2-naphthamide (75 mg, 0.18 mmol, 1 eq) in MeCN (3 mL) was added K2CO3 (62.5 mg, 0.45 mmol, 2.5 eq) and 2-bromo-1,1-difluoroethane (39.4 mg, 0.27 mmol, 2.6 uL, 1.5 eq). The mixture was stirred at 70° C. for 16 hr. The reaction mixture was diluted with H2O (30 mL) and stirred for 5 min. The aqueous phase was extracted with EA (15 mL*3). The combined organic phase was washed with brine (20 mL), dried with anhydrous Na2SO4, filtered and concentrated in vacuum. The residue was purified by prep-HPLC (column: Waters Xbridge C18 150*50 mm*10 um; mobile phase: [water (0.04% NH3H2O)-ACN]; B %: 51%-81%, 11 min) to afford the title compound (26.8 mg, 54.9 umol, 30.33% yield) as a white solid. LCMS (ESI): RT=0.796 min, mass calcd for C25H23F5N2O2 478.17, m/z found 479.3 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ 8.51 (s, 1H), 8.44 (d, J=8.3 Hz, 1H), 8.02-7.90 (m, 3H), 7.74 (d, J=8.8 Hz, 2H), 7.63 (t, J=7.9 Hz, 1H), 7.32 (d, J=7.0 Hz, 1H), 7.15 (d, J=8.5 Hz, 2H), 6.09-5.75 (m, 1H), 4.32-4.19 (m, 1H), 3.34 (t, J=6.8 Hz, 2H), 3.11-2.95 (m, 2H), 2.76 (m, 2H), 2.63-2.52 (m, 2H), 1.09 (d, J=6.5 Hz, 3H).
8
Synthesis of Fluorinated Naphthamide Derivative
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Example 94
To a solution of (R)—N-(1-(azetidin-3-yl)ethyl)-5-(4-(trifluoromethyl)phenoxy)-2-naphthamide (50 mg, 0.12 mmol, 1 eq), KI (2.0 mg, 12.1 umol, 0.1 eq) and K2CO3 (50.0 mg, 0.36 mmol, 3 eq) in ACN (2 mL) at 30° C. was added 2-bromo-1,1-difluoroethane (26.2 mg, 0.18 mmol, 1.5 eq), and the mixture was stirred at 70° C. for 16 h. The reaction mixture was filtered to remove the solid and the filtrate was concentrated under reduced pressure to give a residue. The residue was purified by prep-HPLC (column: Waters Xbridge C18 150*50 mm*10 um; mobile phase: [water (0.04% NH3H2O)-ACN]; B %: 52%-82%, 11 min) to give the title compound (19.9 mg, 41.2 umol, 34.1% yield) as a white solid. LCMS (ESI): RT=0.801 min, mass calc. for C25H23F5N2O2 478.17, m/z found 479.0 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ 8.51 (s, 1H), 8.44 (d, J=8.3 Hz, 1H), 8.02-7.91 (m, 3H), 7.74 (d, J=8.8 Hz, 2H), 7.63 (t, J=7.9 Hz, 1H), 7.32 (d, J=7.5 Hz, 1H), 7.15 (d, J=8.6 Hz, 2H), 6.10-5.76 (m, 1H), 4.32-4.20 (m, 1H), 3.35 (br d, J=3.6 Hz, 2H), 3.06 (t, J=6.8 Hz, 1H), 2.98 (t, J=6.8 Hz, 1H), 2.76 (dt, J=4.2, 16.2 Hz, 2H), 2.62-2.55 (m, 1H), 1.09 (d, J=6.6 Hz, 3H).
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