1188
Vol. 53, No. 9
(NH), 1652 (CO) cmꢁ1 1H-NMR (DMSO-d6) d: 2.97—3.03 (dd, 1H,
.
(NH), 1649 (CO) cmꢁ1
.
1H-NMR (DMSO-d6) d: 2.06 (s, 6H, –CH3ꢀ2),
Jꢃ15.25, 8.34 Hz, one proton of furan–CH2–), 3.07—3.14 (dd, 1H,
Jꢃ15.11, 5.76 Hz, one proton of furan–CH2–), 4.12 (s, 2H, –CH2Cl), 4.70—
4.76 (td, 1H, Jꢃ8.10, 5.92 Hz, –CH2CH–), 6.16—6.17 (dd, 1H, Jꢃ3.17,
0.72 Hz, furan-3H), 6.34—6.35 (dd, 1H, Jꢃ3.17, 1.87 Hz, furan-4H), 7.49—
7.50 (d, 2H, Jꢃ9.03 Hz, benzene-3,5H), 7.51—7.52 (dd, 1H, Jꢃ1.86,
0.86 Hz, furan-5H), 7.55—7.58 (d, 2H, Jꢃ9.04 Hz, benzene-2,6H), 8.64—
8.66 (d, 1H, Jꢃ7.95 Hz, –NHCOCH2Cl), 10.33 (s, 1H, –CONH–). Anal.
Calcd for C15H14BrClN2O3: C, 46.71; H, 3.66; N, 7.27. Found: C, 46.57; H,
3.57; N, 7.21.
2.99—3.05 (dd, 1H, Jꢃ15.13, 8.50 Hz, one proton of furan–CH2–), 3.16—
3.22 (dd, 1H, Jꢃ15.23, 5.95 Hz, one proton of furan–CH2–), 4.12 (s, 2H,
–CH2Cl), 4.76—4.82 (td, 1H, Jꢃ7.42, 5.99 Hz, –CH2CH–), 6.22 (d, 1H,
Jꢃ3.02 Hz, furan-3H), 6.37—6.38 (dd, 1H, Jꢃ3.09, 1.89 Hz, furan-4H),
7.05—7.07 (m, 3H, benzene-3,4,5H), 7.55 (bd, 1H, Jꢃ1.09 Hz, furan-5H),
8.62—8.64 (d, 1H, Jꢃ7.92 Hz, –NHCOCH2Cl), 9.53 (s, 1H, –CONH–).
Anal. Calcd for C17H19ClN2O3: C, 60.98; H, 5.72; N, 8.37. Found: C, 61.18;
H, 5.66; N, 8.42.
2-(2-Chloroacetamido)-3-(furan-2-yl)-N-(thiazol-2-yl)propanamide
(17a) 60% yield, mp 145—148 °C, IR (single bounce ART): 3361 (NH),
2-(2-Chloroacetamido)-N-(2-ethylphenyl)-3-(furan-2-yl)propanamide
(16k) 59% yield, mp 169—171 °C, IR (single bounce ART): 3265 (NH),
1669 (CO) cmꢁ1 1H-NMR (DMSO-d6) d: 3.02—3.08 (dd, 1H, Jꢃ8.47,
.
1648 (CO) cmꢁ1 1H-NMR (DMSO-d6) d: 1.06—1.10 (t, 3H, Jꢃ7.53 Hz,
.
15.33 Hz, one proton of furan–CH2–), 3.13—3.18 (dd, 1H, Jꢃ5.63,
15.24 Hz, one proton of furan–CH2–), 4.13 (s, 2H, –CH2Cl), 4.81—4.87 (td,
1H, Jꢃ5.54, 8.0 Hz, –CH2CH–), 6.17—6.18 (bd, 1H, Jꢃ3.15 Hz, furan-3H),
6.34—6.35 (dd, 1H, Jꢃ1.88, 3.15 Hz, furan-4H), 7.24—7.25 (d, 1H,
Jꢃ3.56 Hz, thiazol-5H), 7.49 (d, 1H, Jꢃ3.56 Hz, thiazol-4H), 7.52 (dd, 1H,
Jꢃ0.79, 1.83 Hz, furan-5H), 8.66—8.68 (d, 1H, Jꢃ7.67 Hz, –CONH–).
Anal. Calcd for C12H12ClN3O3S: C, 45.93; H, 3.86; N, 13.40. Found: C,
45.71; H, 3.87; N, 13.29.
–CH2CH3), 2.48—2.54 (q, 2H, Jꢃ7.49 Hz, –CH2CH3), 3.00—3.06 (dd, 1H,
Jꢃ15.24, 8.10 Hz, one proton of furan–CH2–), 3.12—3.18 (dd, 1H,
Jꢃ15.22, 6.05 Hz, one proton of furan–CH2–), 4.13 (s, 2H, –CH2Cl), 4.79—
4.85 (td, 1H, Jꢃ8.03, 6.03 Hz, –CH2CH–), 6.20—6.21 (bd, 1H, Jꢃ2.93 Hz,
furan-3H), 6.37—6.38 (dd, 1H, Jꢃ3.11, 1.89 Hz, furan-4H), 7.15—7.27 (m,
4H, benzene-3,4,5,6H), 7.55 (bd, 1H, furan-5H), 8.59—8.61 (d, 1H,
Jꢃ8.10 Hz, –NHCOCH2Cl), 9.55 (s, 1H, –CONH–). Anal. Calcd for
C17H19ClN2O3: C, 60.98; H, 5.72; N, 8.37. Found: C, 60.79; H, 5.74; N,
8.41.
2-(2-Chloroacetamido)-N-(5-bromothiazol-2-yl)-3-(furan-2-yl)-
propanamide (17b) 64% yield, mp 182—184 °C, IR (single bounce
ART): 3246 (NH), 1662 (CO) cmꢁ1 1H-NMR (DMSO-d6) d: 3.02—3.08
.
2-(2-Chloroacetamido)-N-(3-ethylphenyl)-3-(furan-2-yl)propanamide
(16l) 60% yield, mp 132—133 °C, IR (single bounce ART): 3282 (NH),
(dd, 1H, Jꢃ15.30, 8.35 Hz, one proton of furan–CH2–), 3.12—3.17 (dd, 1H,
Jꢃ15.32, 5.66 Hz, one proton of furan–CH2–), 4.12 (s, 2H, –CH2Cl), 4.78—
4.84 (td, 1H, Jꢃ7.89, 5.54 Hz, –CH2CH–), 6.16—6.17 (dd, 1H, Jꢃ3.20,
0.77 Hz, furan-3H), 6.34—6.35 (dd, 1H, Jꢃ3.18, 1.87 Hz, furan-4H), 7.51—
7.52 (dd, 1H, Jꢃ1.87, 0.85 Hz, furan-5H), 7.59 (s, 1H, thiazol-4H), 8.69—
8.71 (d, 1H, Jꢃ7.56 Hz, –CONH–). Anal. Calcd for C12H11BrClN3O3S: C,
36.70; H, 2.82; N, 10.70. Found: C, 36.90; H, 2.83; N, 10.58.
1691 and 1649 (CO) cmꢁ1 1H-NMR (DMSO-d6) d: 1.15—1.19 (t, 3H,
.
Jꢃ7.59 Hz, –CH2CH3), 2.54—2.60 (q, 2H, Jꢃ7.57 Hz, –CH2CH3), 2.96—
3.02 (dd, 1H, Jꢃ15.24, 8.39 Hz, one proton of furan–CH2–), 3.09—3.14 (dd,
1H, Jꢃ15.24, 5.74 Hz, one proton of furan–CH2–), 4.12 (d, 2H, Jꢃ0.43 Hz,
–CH2Cl), 4.71—4,76 (td, 1H, Jꢃ8.13, 5.82 Hz, –CH2CH–), 6.17—6.18 (dd,
1H, Jꢃ3.17, 0.70 Hz, furan-3H), 6.34—6.35 (dd, 1H, Jꢃ3.17, 1.87 Hz,
furan-4H), 6.91—6.93 (bd, 1H, benzene-4H), 7.19—7.23 (t, 1H, Jꢃ7.80 Hz,
benzene-5H), 7.39—7.41 (m, 1H, benzene-6H), 7.44 (s, 1H, benzene-2H),
7.52—7.53 (dd, 1H, Jꢃ1.85, 0.83 Hz, furan-5H), 8.59—8.60 (d, 1H,
Jꢃ7.99 Hz, –NHCOCH2Cl), 10.12 (s, 1H, –CONH–). Anal. Calcd for
C17H19N2O3: C, 60.98; H, 5.72; N, 8.37. Found: C, 60.96; H, 5.74; N, 8.45.
2-(2-Chloroacetamido)-N-(4-ethylphenyl)-3-(furan-2-yl)propanamide
(16m) 74% yield, mp 177—178 °C, IR (single bounce ART): 3278 (NH),
2-(2-Chloroacetamido)-3-(furan-2-yl)-N-(5-nitrothiazol-2-yl)-
propanamide (17c) 53% yield, mp 181—183 °C, IR (single bounce ART):
3208 (NH), 1666 (CO) cmꢁ1. H-NMR (DMSO-d6) d: 3.05—3.11 (dd, 1H,
1
Jꢃ15.36, 8.47 Hz, one proton of furan–CH2–), 3.16—3.21 (dd, 1H,
Jꢃ15.31, 5.54 Hz, one proton of furan–CH2–), 4.13 (s, 2H, –CH2Cl), 4.80—
4.86 (m, 1H, –CH2CH–), 6.18—6.19 (bd, 1H, Jꢃ3.18 Hz, furan-3H), 6.35—
6.36 (dd, 1H, Jꢃ3.17, 1.87 Hz, furan-4H), 7.52—7.53 (dd, 1H, Jꢃ1.86,
0.85 Hz, furan-5H), 8.64 (s, 1H, thiazol-4H), 8.78—8.80 (d, 1H, Jꢃ7.16 Hz,
–CONH–). Anal. Calcd for C12H11ClN4O5S: C, 40.17; H, 3.09; N, 15.62.
Found: C, 40.33; H, 3.26; N, 15.75.
1650 (CO) cmꢁ1 1H-NMR (DMSO-d6) d: 1.13—1.17 (t, 3H, Jꢃ7.57 Hz,
.
–CH2CH3), 2.52—2.58 (q, 2H, Jꢃ7.56 Hz, –CH2CH3), 2.96—3.02 (dd, 1H,
Jꢃ15.10, 8.28 Hz, one proton of furan–CH2–), 3.08—3.13 (dd, 1H,
Jꢃ15.29, 5.95 Hz, one proton of furan–CH2–), 4.12 (s, 2H, –CH2Cl), 4.71—
4.76 (td, 1H, Jꢃ8.08, 6.00 Hz, –CH2CH–), 6.16—6.17 (d, 1H, Jꢃ3.12 Hz,
furan-3H), 6.34—6.35 (dd, 1H, Jꢃ3.06, 1.87 Hz, furan-4H), 7.13—7.15 (d,
2H, Jꢃ8.42 Hz, benzene-3,5H), 7.47—7.49 (d, 2H, Jꢃ8.44 Hz, benzene-
2.6H), 7.52 (bd, 1H, furan-5H), 8.59—8.61 (d, 1H, Jꢃ8.16 Hz,
–NHCOCH2Cl), 10.10 (s, 1H, –CONH–). Anal. Calcd for C17H19ClN2O3: C,
60.98; H, 5.72; N, 8.37. Found: C, 60.88; H, 5.73; N, 8.42.
2-(2-Chloroacetamido)-3-(furan-2-yl)-N-(4-methylthiazol-2-yl)-
propanamide (17d) 65% yield, mp 116—118 °C, IR (single bounce
ART): 3197 and 3067 (NH), 1685 and 1659 (CO) cmꢁ1. H-NMR (DMSO-
1
d6) d: 2.26 (d, 3H, Jꢃ0.98 Hz, –CH3), 3.01—3.07 (dd, 1H, Jꢃ15.31,
8.37 Hz, one proton of furan–CH2–), 3.11—3.17 (dd, 1H, Jꢃ15.30, 5.54 Hz,
one proton of furan–CH2–), 4.12 (s, 2H, –CH2Cl), 4.77—4.82 (td, 1H,
Jꢃ7.98, 5.61 Hz, –CH2CH–), 6.16—6.17 (bd, 1H, Jꢃ2.70 Hz, furan-3H),
6.34—6.35 (dd, 1H, Jꢃ3.17, 1.88 Hz, furan-4H), 6.78 (d, 1H, Jꢃ1.07 Hz,
thiazol-5H), 7.52 (dd, 1H, Jꢃ1.85, 0.80 Hz, furan-5H), 8.62—8.64 (d, 1H,
Jꢃ7.57 Hz, –CONH–). Anal. Calcd for C13H14ClN3O3S: C, 47.63; H, 4.31;
N, 12.82. Found: C, 47.36; H, 4.10; N, 12.66.
2-(2-Chloroacetamido)-N-(2,6-diethylphenyl)-3-(furan-2-yl)propan-
amide (16n) 57% yield, mp 184—185 °C, IR (single bounce ART): 3259
(NH), 1645 (CO) cmꢁ1 1H-NMR (DMSO-d6) d: 1.02—1.06 (t, 6H,
.
Jꢃ7.52 Hz, –CH3ꢀ2), 2.40—2.42 (dq, 4H, –CH2CH3ꢀ2), 2.98—3.04 (dd,
1H, Jꢃ15.09, 8.30 Hz, one proton of furan–CH2–), 3.16—3.22 (dd, 1H,
Jꢃ15.17, 6.11 Hz, one proton of furan–CH2–), 4.11 (s, 2H, –CH2Cl), 4.81—
4.86 (td, 1H, Jꢃ8.24, 6.11 Hz, –CH2CH–), 6.23—6.24 (bd, 1H, Jꢃ2.90 Hz,
furan-3H), 6.38—6.39 (dd, 1H, Jꢃ3.09, 1.89 Hz, furan-4H), 7.06—7.19 (m,
3H, benzene-3,4,5H), 7.56 (bd, 1H, furan-5H), 8.67—8.69 (d, 1H,
Jꢃ8.29 Hz, –NHCOCH2Cl), 9.54 (s, 1H, –CONH–), furan-5H), 9.54 (s, 1H,
–CONH–). Anal. Calcd for C19H23ClN2O3: C, 62.89; H, 6.39; N, 7.72.
Found: C, 62.72; H, 6.24; N, 7.80.
2-(2-Chloroacetamido)-3-(furan-2-yl)-N-(5-methylthiazol-2-yl)-
propanamide (17e) 78% yield, mp 185—187 °C, IR (single bounce ART):
3231 (NH), 1657 (CO) cmꢁ1 1H-NMR (DMSO-d6) d: 2.34 (d, 3H,
.
Jꢃ1.20 Hz, –CH3), 3.00—3.06 (dd, 1H, Jꢃ15.23, 8.30 Hz, one proton of
furan–CH2–), 3.10—3.16 (dd, 1H, Jꢃ15.29, 5.74 Hz, one proton of
furan–CH2–), 4.12 (s, 2H, –CH2Cl), 4.79—4.84 (td, 1H, Jꢃ7.97, 5.66 Hz,
–CH2CH–), 6.16 (bd, 1H, Jꢃ3.13 Hz, furan-3H), 6.34—6.35 (dd, 1H,
Jꢃ3.16, 1.87 Hz, furan-4H), 7.15 (d, 1H, Jꢃ1.28 Hz, thiazol-4H), 7.51—
7.52 (dd, 1H, Jꢃ1.82, 0.78 Hz, furan-5H), 8.64—8.66 (d, 1H, Jꢃ7.69 Hz,
–CONH–). Anal. Calcd for C13H14ClN3O3S: C, 47.63; H, 4.31; N, 12.82.
Found: C, 47.83; H, 4.33; N, 12.71.
2-(2-Chloroacetamido)-N-(2-ethyl-6-methylphenyl)-3-(furan-2-yl)-
propanamide (16o) 46% yield, mp 175—178 °C, IR (single bounce
ART): 3265 (NH), 1647 (CO) cmꢁ1. 1H-NMR (DMSO-d6) d: 1.02—1.06 (t,
3H, Jꢃ7.54 Hz, –CH2CH3), 2.05 (s, 3H, –CH3), 2.39—2.45 (q, 2H,
Jꢃ7.46 Hz, –CH2CH3), 2.99—3.05 (dd, 1H, Jꢃ15.25, 5.96 Hz, one proton
of furan–CH2–), 3.16—3.22 (dd, 1H, Jꢃ15.25, 5.96 Hz, one proton of
furan–CH2–), 4.11 (s, 2H, –CH2Cl), 4.79—4.84 (td, 1H, Jꢃ8.21, 6.04 Hz,
–CH2CH–), 6.22—6.23 (bd, 1H, Jꢃ3.06 Hz, furan-3H), 6.38—6.39 (dd, 1H,
Jꢃ3.07, 1.90 Hz, furan-4H), 7.05—7.14 (m, 3H, benzene-3,4,5H), 7.55 (bd,
1H, Jꢃ1.47 Hz, furan-5H), 8.63—8.65 (d, 1H, Jꢃ8.16 Hz, –NHCOCH2Cl),
9.52 (s, 1H, –CONH–). Anal. Calcd for C18H21ClN2O3: C, 61.98; H, 6.07; N,
8.03. Found: C, 61.94; H, 5.97; N, 8.02.
2-(2-Chloroacetamido)-3-(furan-2-yl)-N-(4,5-dimethylthiazol-2-yl)-
propanamide (17f) 60% yield, mp 128—130 °C, IR (single bounce ART):
3180 (NH), 1697 and 1654 (CO) cmꢁ1. 1H-NMR (DMSO-d6) d: 2.15 (s, 3H,
–CH3), 2.23 (s, 3H, –CH3), 2.99—3.05 (dd, 1H, Jꢃ15.31, 8.22 Hz, one pro-
ton of furan–CH2–), 3.10—3.15 (dd, 1H, Jꢃ15.26, 5.33 Hz, one proton of
furan–CH2–), 4.12 (s, 2H, –CH2Cl), 4.75—4.81 (td, 1H, Jꢃ7.94, 5.73 Hz,
–CH2CH–), 6.14—6.15 (bd, 1H, Jꢃ2.69 Hz, furan-3H), 6.33—6.35 (dd, 1H,
Jꢃ3.16, 1.87 Hz, furan-4H), 7.51—7.52 (dd, 1H, Jꢃ1.85, 0.80 Hz, furan-
5H), 8.61—8.63 (d, 1H, Jꢃ7.74 Hz, –CONH–). Anal. Calcd for
C14H16ClN3O3S: C, 49.19; H, 4.72; N, 12.30. Found: C, 49.27; H, 4.61; N,
12.21.
2-(2-Chloroacetamido)-3-(furan-2-yl)-N-(2,6-dimethylphenyl)propan-
amide (16p) 55% yield, mp 181—183 °C, IR (single bounce ART): 3265