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Organic & Biomolecular Chemistry
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Journal Name
1-(3-(4-Chlorophenoxy)propyl)-6-(4-(trifluoromethyl)phenyl)-1,6-
ARTICLE
1
DOI: 10.1039/C6OB01350C
dihydro-1,3,5-triazine-2,4-diamine hydrochloride (11b). Prepared as a white crystalline solid (22 mg, 4%). m.p. 194 – 196 °C; H NMR
from 3-(4-chlorophenoxy)propan-1-amine and α,α,α,-trifluoro-p- (400 MHz, CD3OD) δ 7.53 – 7.45 (2 H, m), 7.36 – 7.29 (2 H, m), 7.29
tolualdehyde, isolated as a white solid (275 mg, 47%). m.p. 227 – – 7.21 (2 H, m), 6.99 – 6.93 (2 H, m), 5.82 (1 H, s), 4.13 – 4.04 (2 H,
1
230 °C; H NMR (400 MHz, CD3OD) δ 7.80 (d, J = 8.2 Hz, 2H), 7.61 (d, m), 3.82 – 3.71 (1 H, m), 3.45 – 3.40 (1 H, m), 2.26 – 2.12 (1 H, m),
J = 8.2 Hz, 2H), 7.32 – 7.26 (m, 2H), 6.97 – 6.91 (m, 2H), 5.91 (s, 1H), 2.12 – 1.99 (1 H, m); 13C NMR (101 MHz, CD3OD) δ 165.7 (d, JC-F
=
4.10 – 3.99 (m, 2H), 3.90 – 3.78 (m, 1H), 3.29 – 3.21 (m, 1H), 2.14 – 247.9 Hz), 160.0, 159.6, 159.5, 137.3 (d, JC-F = 3.2 Hz), 131.3, 130.5
1.82 (m, 2H); 13C NMR (101 MHz, CD3OD) δ 159.3, 158.8, 158.6, (d, JC-F = 8.7 Hz), 127.7, 118.1 (d, JC-F = 22.2 Hz), 117.8, 70.2, 66.9,
144.5, 132.8 (q, JC-F = 32.5 Hz), 130.4, 128.1, 127.4 (q, JC-F = 3.8 Hz), 46.4, 28.4; HRMS (ESI) found (M + H)+ 376.1334, C18H2035ClFN5O
126.9, 125.3 (q, JC-F = 271.5 Hz), 117.0, 69.1, 66.1, 46.1, 27.2; HRMS requires 376.1340; compound purity (UPLC) 93.1%.
(ESI) found (M + H)+ 426.1302, C19H2035ClF3N5Orequires 426.1308;
compound purity (UPLC) 99.7%.
1-(3-(4-Chlorophenoxy)propyl)-6-(2-fluorophenyl)-1,6-dihydro-
1,3,5-triazine-2,4-diamine hydrochloride (11g). Prepared from 3-(4-
chlorophenoxy)propan-1-amine and 2-fluorobenzaldehyde, isolated
as an off-white solid (107 mg, 20%). m.p. 221 – 224 °C; 1H NMR (400
MHz, CD3OD) δ 7.54 – 7.43 (m, 1H), 7.35 (tt, J = 7.6, 2.0 Hz, 1H),
7.30 – 7.19 (m, 4H), 6.96 – 6.86 (m, 2H), 6.08 (d, J = 1.8 Hz, 1H), 4.09
– 4.00 (m, 2H), 3.81 – 3.69 (m, 1H), 3.41 – 3.30 (m, 1H), 2.23 – 2.08
(m, 1H), 2.08 – 1.95 (m, 1H); 13C NMR (101 MHz, CD3OD) δ 162.6 (d,
JC-F = 247.6 Hz), 160.1, 159.6, 159.5, 133.9 (d, JC-F = 8.6 Hz), 131.3,
1-(3-(4-Chlorophenoxy)propyl)-6-(4-methoxyphenyl)-1,6-dihydro-
1,3,5-triazine-2,4-diamine hydrochloride (11c). Prepared from 3-(4-
chlorophenoxy)propan-1-amine and 4-methoxybenzaldehyde,
isolated as an off-white solid (25 mg, 4%). 1H NMR (400 MHz,
CD3OD) δ 7.34 – 7.30 (m, 2H), 7.27 – 7.23 (m, 2H), 6.99 – 6.95 (m,
2H), 6.90 – 6.86 (m, 2H), 5.68 (s, 1H), 4.04 – 3.96 (m, 2H), 3.80 (d, J
= 0.8 Hz, 3H), 3.70 – 3.59 (m, 1H), 3.38 – 3.25 (m, 1H), 2.13 – 2.03
(m, 1H), 2.02 – 1.91 (m, 1H); 13C NMR (101 MHz, CD3OD) δ 162.4,
159.2, 158.7, 158.6, 132.0, 130.4, 129.0, 126.9, 117.0, 115.7, 69.8,
66.1, 55.9, 45.3, 27.6; HRMS (ESI) found (M + H)+ 388.1541,
C19H2335ClN5O2 requires 388.1540; compound purity (UPLC) 95.7%.
129.6 (d, JC-F = 3.1 Hz), 127.8 (d, JC-F = 12.7 Hz), 127.8, 127.1 (d, JC-F
=
3.6 Hz), 118.3 (d, JC-F = 21.4 Hz), 117.9, 66.9, 66.0 (d, JC-F = 3.9 Hz),
46.5, 28.5; HRMS (ESI) found (M + H)+ 376.1341, C18H2035ClFN5O
requires 376.1340; compound purity (UPLC) 96.7%.
6-(4-Chloro-3-fluorophenyl)-1-(3-(4-chlorophenoxy)propyl)-1,6-
1-(3-(4-Chlorophenoxy)propyl)-6-(2-(trifluoromethyl)phenyl)-1,6-
dihydro-1,3,5-triazine-2,4-diamine hydrochloride (11h). Prepared
from 3-(4-chlorophenoxy)propan-1-amine and α,α,α,-trifluoro-o-
tolualdehyde, isolated as a white crystalline solid (95 mg, 11%).
m.p. 230 – 234 °C; 1H NMR (400 MHz, CD3OD) δ 7.83 (dd, J = 15.7,
7.6 Hz, 2H), 7.68 (t, J = 7.4 Hz, 2H), 7.28 (d, J = 8.7 Hz, 2H), 6.90 (d, J
= 8.8 Hz, 2H), 6.16 (s, 1H), 4.12 – 3.97 (m, 2H), 3.70 (ddd, J = 15.5,
7.7, 5.5 Hz, 1H), 3.27 – 3.16 (m, 1H), 2.25 – 2.11 (m, 1H), 2.08 – 1.94
(m, 1H); 13C NMR (101 MHz, CD3OD) δ 160.3, 159.4, 159.1, 140.2,
dihydro-1,3,5-triazine-2,4-diamine hydrochloride (11d). Prepared
from
3-(4-chlorophenoxy)propan-1-amine
and
4-chloro-3-
fluorobenzaldehyde, isolated as an off-white solid (118 mg, 18%).
m.p. 215 – 218 °C; 1H NMR (400 MHz, CD3OD) δ 7.91 – 7.81 (m, 2H),
7.76 – 7.67 (m, 2H), 7.51 – 7.41 (m, 1H), 7.14 – 7.09 (m, 1H), 6.97 –
6.85 (m, 1H), 6.19 (s, 1H), 4.17 – 4.02 (m, 2H), 3.80 – 3.66 (m, 1H),
3.31 – 3.17 (m, 1H), 2.27 – 2.14 (m, 1H), 2.12 – 1.96 (m, 1H).; 13C
NMR (101 MHz, CD3OD) δ 160.4 (d, JC-F = 250.0 Hz), 160.1, 159.6,
159.5, 142.4 (d, JC-F = 5.5 Hz), 133.7, 131.2, 127.7, 125.0 (d, JC-F = 3.8
Hz), 124.1 (d, JC-F = 17.8 Hz), 117.9, 116.6 (d, JC-F = 22.4 Hz), 69.4,
136.0, 132.5, 131.2, 129.6, 129.4 (q, JC-F = 30.7 Hz), 128.4 (q, JC-F
=
5.7 Hz), 127.7, 126.3 (q, JC-F = 273.6 Hz), 117.7, 67.0 (q, JC-F = 2.3 Hz),
+
H)+ 410.0947,
66.8, 46.7, 28.1; HRMS (ESI) found (M
+
H)+ 426.1239,
67.0, 47.0, 28.6; HRMS (ESI) found (M
C18H1935Cl2FN5O requires 410.0951; compound purity (UPLC) 94.3%.
C19H2035ClF3N5O requires 426.1308; compound purity (UPLC) 97.4%.
1-(3-(4-Chlorophenoxy)propyl)-6-(3-chlorophenyl)-1,6-dihydro-
1,3,5-triazine-2,4-diamine hydrochloride (11e). Prepared from 3-
(4-chlorophenoxy)propan-1-amine and 3-chlorobenzaldehyde,
1-(3-(4-Chlorophenoxy)propyl)-6-(4-chlorophenyl)-1,6-dihydro-
1,3,5-triazine-2,4-diamine hydrochloride (11i). Prepared from 3-(4-
chlorophenoxy)propan-1-amine and 4-chlorobenzaldehyde, isolated
as a white crystalline solid (58 mg, 11%). m.p. 226 – 228 °C; 1H NMR
(400 MHz, CD3OD) δ 7.51 – 7.42 (m, 2H), 7.41 – 7.33 (m, 2H), 7.31 –
7.21 (m, 2H), 6.94 – 6.86 (m, 2H), 5.77 (s, 1H), 4.06 – 3.99 (m, 2H),
3.73 (ddd, J = 15.3, 7.7, 5.8 Hz, 1H), 3.38 – 3.32 (m, 1H), 2.19 – 2.07
(m, 1H), 2.06 – 1.94 (m, 1H); 13C NMR (101 MHz, CD3OD) δ 159.2,
158.7, 158.6, 139.1, 136.8, 130.6, 130.4, 129.1, 126.9, 117.0, 69.3,
1
isolated as an off-white solid (33 mg, 6%). m.p. 216 – 218 °C; H
NMR (400 MHz, CD3OD) δ 7.48 – 7.43 (m, 2H), 7.41 – 7.38 (m, 1H),
7.34 – 7.29 (m, 1H), 7.29 – 7.23 (m, 2H), 6.94 – 6.87 (m, 2H), 5.76 (s,
1H), 4.07 – 4.00 (m, 2H), 3.76 (ddd, J = 15.4, 7.6, 5.9 Hz, 1H), 3.39 –
3.32 (m, 1H), 2.20 – 2.09 (m, 1H), 2.09 – 1.96 (m, 1H); 13C NMR (101
MHz, CD3OD) δ 159.2, 158.7, 158.6, 142.6, 136.3, 132.2, 131.0,
130.4, 127.4, 126.9, 125.7, 117.0, 69.2, 66.0, 45.8, 27.7; HRMS (ESI)
found (M + H)+ 392.1041, C18H2035Cl2N5O requires 392.1045;
compound purity (UPLC) 99.7%.
66.1, 45.7, 27.6; HRMS (ESI) found (M
C18H2035Cl2N5O requires 392.1045; compound purity (UPLC) 98.5%.
+
H)+ 392.1017,
6-(3-Chloro-2-fluorophenyl)-1-(3-(4-chlorophenoxy)propyl)-1,6-
1-(3-(4-Chlorophenoxy)propyl)-6-(4-fluorophenyl)-1,6-dihydro-
dihydro-1,3,5-triazine-2,4-diamine hydrochloride (11j). Prepared
1,3,5-triazine-2,4-diamine hydrochloride (11f). Prepared from 3-(4-
from
3-(4-chlorophenoxy)propan-1-amine
and
3-chloro-2-
This journal is © The Royal Society of Chemistry 20xx
J. Name., 2013, 00, 1-3 | 9
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