2H), 2.20 (s, 6H), 1.50-1.33 (m, 2H), 1.28-1.21 (m, 2H); MS-
(ESI) m/z: [M+H]+, 488; HRMS: Calcd. for C27H27FN5O3:
488.2094; found: 488.2088; . HPLC analysis: retention time =
14.4 min; peak area, 99.38%.
found: 477.1860; HPLC analysis: retention time = 12.5 min; peak
area, 99.47%.
4.2.1.17. (S)-3-{1-(4-Fluorophenyl)-5-[5-(2-fluorophenyl)-4H-
1,2,4-triazol-3-yl]-1,3-dihydroisobenzofuran-1-yl}-N,N-dime
thylpropan-1-amine (76) Colorless crystalline solid; Yield: 4.29
4.2.1.11. (S)-3-{1-(4-Fluorophenyl)-5-[5-(o-tolyl)-4H-1,2,4-tria
zol-3-yl]-1,3-dihydroisobenzofuran-1-yl}-N,N-dimethylprop
an-1-amine (70) Brown crystalline solid; Yield: 4.12 g (90%);
o
1
g (93%); mp 153-156 C; H NMR (300 MHz, DMSO-d6) δH:
7.87 (br s, 1NH), 7.78-7.73 (m, 5H), 7.60-7.56 (m, 3H), 7.17-
7.12 (m, 3H), 5.21-5.11 (m, 2H), 2.17-2.14 (m, 4H), 2.02 (s, 6H),
1.29-1.23 (m, 2H); MS-(ESI) m/z: [M+H]+, 461; HRMS: Calcd.
for C27H27F2N4O: 461.2150; found: 461.2157; HPLC analysis:
retention time = 13.5 min; peak area, 99.67%.
o
1
mp 109-111 C; H NMR (300 MHz, DMSO-d6) δH: 8.41 (br s,
1NH), 7.77-7.55 (m, 7H), 7.26-7.14 (m, 4H), 5.33-5.02 (m, 2H),
3.30-3.21 (m, 2H), 2.66-2.63 (m, 2H), 2.47 (s, 6H), 2.30 (s, 3H),
1.39-1.20 (m, 2H); MS-(ESI) m/z: [M+H]+, 457; HRMS: Calcd.
for C28H30FN4O: 457.2400; found: 457.2408; . HPLC analysis:
retention time = 15.1 min; peak area, 99.15%.
4.2.1.18. (S)-3-{1-(4-Fluorophenyl)-5-[5-(3-fluorophenyl)-4H-
1,2,4-triazol-3-yl]-1,3-dihydroisobenzofuran-1-yl}-N,N-dime
thylpropan-1-amine (77) Colorless crystalline solid; Yield: 4.0
4.2.1.12. (S)-3-{1-(4-Fluorophenyl)-5-[5-(m-tolyl)-4H-1,2,4-tri
azol-3-yl]-1,3-dihydroisobenzofuran-1-yl}-N,N-dimethylprop
an-1-amine (71) Brown crystalline solid; Yield: 4.26 g (93%);
o
1
g (87%); mp 187-189 C; H NMR (300 MHz, DMSO-d6) δH:
8.24 (br s, 1NH), 7.78-7.68 (m, 5H), 7.60-7.56 (m, 3H), 7.18 (t, J
= 9.0 Hz, 3H), 5.22-5.10 (m, 2H), 2.19-2.13 (m, 2H), 2.04 (s,
6H), 1.37-1.24 (m, 2H), 1.22-1.14 (m, 2H); MS-(ESI) m/z:
[M+H]+, 461; HRMS: Calcd. for C27H27F2N4O: 461.2151; found:
461.2155; HPLC analysis: retention time = 13.4 min; peak area,
99.47%.
o
1
mp 125-127 C; H NMR (300 MHz, DMSO-d6) δH: 8.13 (br s,
1NH), 7.79-7.71 (m, 5H), 7.58-7.54 (m, 3H), 7.17-7.11 (m, 3H),
5.20-5.10 (m, 2H), 2.82 (t, J = 5.7 Hz, 2H), 2.61 (s, 6H), 2.43-
2.42 (m, 2H), 2.35 (s, 3H), 2.24-2.13 (m, 2H); MS-(ESI) m/z:
[M+H]+, 457; HRMS: Calcd. for C28H30FN4O: 457.2402; found:
457.2411; . HPLC analysis: retention time = 15.3 min; peak area,
99.03%.
4.2.1.19. (S)-3-{1-(4-Fluorophenyl)-5-[5-(4-fluorophenyl)-4H-
1,2,4-triazol-3-yl]-1,3-dihydroisobenzofuran-1-yl}-N,N-dime
thylpropan-1-amine (78) Colorless crystalline solid; Yield: 4.38
4.2.1.13. (S)-3-{1-(4-Fluorophenyl)-5-[5-(p-tolyl)-4H-1,2,4-tria
zol-3-yl]-1,3-dihydroisobenzofuran-1-yl}-N,N-dimethylprop
an-1-amine (72) Brown crystalline solid; Yield: 4.37 g (96%);
o
1
g (95%); mp 163-165 C; H NMR (300 MHz, DMSO-d6) δH:
8.06 (br s, 1NH), 7.77-7.71 (m, 5H), 7.59-7.54 (m, 3H), 7.16 (t, J
= 8.7 Hz, 3H), 5.20-5.08 (m, 2H), 2.14 (t, J = 7.6 Hz, 2H), 1.99
(s, 6H), 1.76-1.74 (m, 2H), 1.27-1.13 (m, 2H); 13C NMR (100
MHz, CD3OD) δC: 163.24, 160.79, 153.15, 149.53, 140.32,
139.59, 131.85, 126.81, 126.73, 125.21, 122.79, 118.66, 115.41,
115.20, 111.68, 91.11, 71.30, 59.36, 45.26, 38.91, 22.07; MS-
(ESI) m/z: [M+H]+, 461; HRMS: Calcd. for C27H27F2N4O:
461.2150; found: 461.2161; HPLC analysis: retention time =
13.2 min; peak area, 99.33%.
o
1
mp 78-80 C; H NMR (300 MHz, DMSO-d6) δH: 7.93 (br s,
1NH), 7.77-7.72 (m, 5H), 7.58-7.55 (m, 3H), 7.15-7.11 (m, 3H),
5.20-5.10 (m, 2H), 3.21-3.15 (m, 2H), 2.49 (s, 3H), 2.13-2.10 (m,
2H), 1.99 (s, 6H), 1.27-1.19 (m, 2H); MS-(ESI) m/z: [M+H]+,
457; HRMS: Calcd. for C28H30FN4O: 457.2407; found: 457.2415;
HPLC analysis: retention time = 15.6 min; peak area, 99.53%.
4.2.1.14. (S)-3-{5-[5-(2-Chlorophenyl)-4H-1,2,4-triazol-3-yl]-
1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-yl}-N,N-dime
thylpropan-1-amine (73) Colorless crystalline solid; Yield: 4.21
4.2.1.20. (S)-3-{5-[5-(2-Bromophenyl)-4H-1,2,4-triazol-3-yl]-
1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-yl}-N,N-dime
thylpropan-1-amine (79) Brownish crystalline solid; Yield: 4.23
o
1
g (88%); mp 211-214 C; H NMR (300 MHz, DMSO-d6) δH:
8.30 (s, 1H), 7.82-7.74 (m, 5H), 7.62-7.57 (m, 3H), 7.21 (t, J =
9.0 Hz, 3H), 5.25-5.14 (m, 2H), 2.45 (s, 6H), 2.23 (t, J = 7.2 Hz,
2H), 1.59-1.40 (m, 2H), 1.36-1.29 (m, 2H); MS-(ESI) m/z:
[M+H]+, 477, 479; HRMS: Calcd. for C27H27ClFN4O: 477.1852;
found: 477.1861; HPLC analysis: retention time = 12.0 min; peak
area, 99.43%.
o
1
g (81%); mp 141-143 C; H NMR (300 MHz, DMSO-d6) δH:
7.87 (br s, 1NH), 7.78-7.71 (m, 5H), 7.58-7.54 (m, 3H), 7.16-
7.10 (m, 3H), 5.20-5.09 (m, 2H), 2.20-2.15 (m, 2H), 2.03 (s, 6H),
1.45-1.33 (m, 2H), 1.27-1.17 (m, 2H); MS-(ESI) m/z: [M+H]+,
521, 523; HRMS: Calcd. for C27H27BrFN4O: 521.1349; found:
521.1357; HPLC analysis: retention time = 14.2 min; peak area,
99.21%.
4.2.1.15. (S)-3-{5-[5-(3-Chlorophenyl)-4H-1,2,4-triazol-3-yl]-
1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-yl}-N,N-dime
thylpropan-1-amine (74) Colorless crystalline solid; Yield: 4.11
4.2.1.21. (S)-3-{5-[5-(3-Bromophenyl)-4H-1,2,4-triazol-3-yl]-
1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-yl}-N,N-dime
thylpropan-1-amine (80) Brownish crystalline solid; Yield: 4.13
o
1
g (86%); mp 233-236 C; H NMR (300 MHz, DMSO-d6) δH:
8.11 (br s, 1NH), 7.73-7.69 (m, 5H), 7.57-7.52 (m, 3H), 7.14 (t, J
= 8.7 Hz, 3H), 5.18-5.07 (m, 2H), 2.00 (s, 6H), 2.14-2.10 (m,
2H), 1.28-1.11 (m, 4H); MS-(ESI) m/z: [M+H]+, 477, 479;
HRMS: Calcd. for C27H27ClFN4O: 477.1855; found: 477.1867;
HPLC analysis: retention time = 12.3 min; peak area, 99.36%.
o
1
g (79%); mp 121-123 C; H NMR (300 MHz, DMSO-d6) δH:
7.76-7.73 (m, 5H), 7.71 (s, 1NH), 7.58-7.54 (m, 3H), 7.16 (t, J =
9.0 Hz, 3H), 5.20-5.08 (m, 2H), 2.14-2.09 (m, 2H), 1.99 (s, 6H),
1.34-1.23 (m, 2H), 1.21-1.19 (m, 2H); MS-(ESI) m/z: [M+H]+,
521, 523; HRMS: Calcd. for C27H27BrFN4O: 521.1351; found:
521.1355; HPLC analysis: retention time = 14.5 min; peak area,
99.38%.
4.2.1.16. (S)-3-{5-[5-(4-Chlorophenyl)-4H-1,2,4-triazol-3-yl]-
1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-yl}-N,N-dime
thylpropan-1-amine (75) Colorless crystalline solid; Yield: 4.31
4.2.1.22. (S)-3-{5-[5-(4-Bromophenyl)-4H-1,2,4-triazol-3-yl]-
1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-yl}-N,N-dime
thylpropan-1-amine (81) Brownish crystalline solid; mp 158-
161 oC; Yield: 4.37 g (84%); 1H NMR (300 MHz, DMSO-d6) δH:
7.85 (br s, 1NH), 7.77-7.71 (m, 5H), 7.59-7.54 (m, 3H), 7.16 (t, J
= 8.7 Hz, 3H), 5.20-5.09 (m, 2H), 2.18-2.14 (m, 2H), 2.04 (s,
6H), 1.33-1.23 (m, 2H), 1.20-1.11 (m, 2H); MS-(ESI) m/z:
o
1
g (91%); mp 280-282 C; H NMR (300 MHz, DMSO-d6) δH:
8.09 (br s, 1NH), 7.81-7.74 (m, 5H), 7.61-7.57 (m, 3H), 7.18 (t, J
= 8.7 Hz, 3H), 5.24-5.13 (m, 2H), 2.90-2.86 (m, 2H), 2.54 (s,
6H), 2.26-2.22 (m, 2H), 1.54-1.38 (m, 2H); MS-(ESI) m/z:
[M+H]+, 477, 479; HRMS: Calcd. for C27H27ClFN4O: 477.1855;