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1-(2’-Methoxy-1’-methyl-ethyl)-1H-benzotriazole-5-carboxylic acid (3b) (B). (0.010g, 11%) HPLC/MS:
(column c) 96%, tr=1.61 min, m/z (ES+): 236 [M+H]+. 1H NMR (CD3OD): δ 8.68 (s, 1H, C(4)-H), 8.18 (dd, 1H,
J1=8.8, J2=1.3, C(6)-H), 7.88 (d, 1H, J=8.8, C(7)-H), 5.35-5.25 (m, 1H, NCH), 3.93 (dd, 1H, J1=10.0, J2=8.4,
CHCHH), 3.85 (dd, 1H, J1=10.0, J2=4.4, CHCHH), 3.25 (s, 3H, OCH3), 1.73 (d, 3H, J=6.8, CH3).
1-(2’-Ethoxy-ethyl)-1H-benzotriazole-5-carboxylic acid (3c) (B). (0.042g, 43%) HPLC/MS: (column c) 97%,
tr=1.64 min, m/z (ES+): 236 [M+H]+. 1H NMR (CD3OD): δ 8.68 (d, 1H, J=0.8, C(4)-H), 8.18 (dd, 1H, J1=8.8,
J2=1.3, C(6)-H), 7.88 (dd, 1H, J1=8.8, J2=0.6, C(7)-H), 4.92 (t, 2H, J=5.2, NCH2), 3.95 (t, 2H, J=5.0, NCH2CH2),
3.44 (q, 2H, J=7.0, CH2CH3), 1.04 (t, 3H, J=7.0, CH3).
1-t-Butyl-1H-benzotriazole-5-carboxylic acid (3d) (B). (0.036g, 33%) HPLC/MS: (column c) 91%, tr=1.93
min, m/z (ES+): 220 [M+H]+.1H NMR (CD3OD): δ 8.68 (dd, 1H, J1=1.5, J2=0.6, C(4)-H), 8.17 (dd, 1H, J1=8.9,
J2=1.5, C(6)-H), 8.07 (dd, 1H, J1=8.8, J2=0.6, C(7)-H), 1.90 (s, 9H, CH3).
1-Pentyl-1H-benzotriazole-5-carboxylic acid (3e) (B). (0.029g, 31%) HPLC/MS: (column c) 95%, tr=2.25 min,
m/z (ES+): 234 [M+H]+.1H NMR (CD3OD): δ 8.69 (d, 1H, J=0.8, C(4)-H), 8.21 (dd, 1H, J1=8.8, J2=1.4, C(6)-H),
7.86 (dd, 1H, J1=8.8, J2=0.6, C(7)-H), 4.76 (t, 2H, J=7.2, NCH2), 2.10-1.95 (m, 2H, NCH2CH2), 1.45-1.25 (m, 4H),
0.90 (t, 3H, J=7.2, CH3).
1-(2’-Ethylsulfanyl-ethyl)-1H-benzotriazole-5-carboxylic acid (3f) (B). (0.015g, 16%) HPLC/MS: (column c)
92%, tr=1.94 min, m/z (ES+): 252 [M+H]+. 1H NMR (CD3OD): δ 8.69 (d, 1H, J=0.8, C(4)-H), 8.21 (dd, 1H, J1=8.8,
J2=1.4, C(6)-H), 7.89 (d, 1H, J=8.8, C(7)-H), 4.95 (t, 2H, J=6.8, NCH2), 3.18 (t, 2H, J=6.8, NCH2CH2), 2.48 (q,
2H, J=7.6, CH2CH3), 1.18 (t, 3H, J=7.4, CH2CH3).
1-(2-Methoxy-ethyl)-1H-benzotriazole-5-carboxylic acid (3g) (B). (0.054g, 59%) HPLC/MS: (column b) 90%,
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tr=1.44 min, m/z (ES+): 222 [M+H]+. H NMR (CD3OD): δ 8.67 (dd, 1H, J1=1.4, J2=0.7, C(4)-H), 8.18 (dd, 1H,
J1=8.8, J2=1.4, C(6)-H), 7.87 (dd, 1H, J1=8.8, J2=0.7, C(7)-H), 4.93 (t, 2H, J=5.1, NCH2), 3.91 (t, 2H, J=5.1,
OCH2), 3.29 (s, 3H, OCH3).
1-(2’-Butyl)-1H-benzotriazole-5-carboxylic acid (3h). (B) (0.026g, 29%) HPLC/MS: (column a) 96%, tr=1.87
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min, m/z (ES+): 220 [M+H]+. H NMR (CD3OD): δ 8.72 (dd, 1H, J1=1.3, J2=0.7, C(4)-H), 8.22 (dd, 1H, J1=8.8,
J2=1.3, C(6)-H), 7.91 (dd, 1H, J1=8.8, J2=0.7, C(7)-H), 5.10-5.00 (m, 1H, NCH), 2.30-2.05 (m, 2H, CH2CH3), 1.75
(d, 3H, J=6.8, CHCH3), 0.85 (t, 3H, J=7.4, CH2CH3).
1-Butyl-1H-benzotriazole-5-carboxylic acid (3i) (C). (0.023g, 25%) HPLC/MS: (column c) 97%, tr=2.01 min,
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m/z (ES+): 220 [M+H]+. H NMR (CD3OD): δ 8.68 (dd, 1H, J1=1.4, J2=0.6, C(4)-H), 8.20 (dd, 1H, J1=8.8, J2=1.4,