Journal of Combinatorial Chemistry, 2010 Vol. 12, No. 1 157
Perfluorophenyl 1-Methyl-4-(4-(4-(1-methyl-5-(2-(pyrro-
lidin-1-yl)ethylcarbamoyl)-1H-pyrrol-3-ylcarbamoyl)ben-
zoyl)benzamido)-1H-pyrrole-2-carboxylate (14{2}). 1H NMR
(400 MHz, CDCl3 and CD3OD): δ 7.99-7.93 (m, 4H, Ar-
H), 7.78 (d, J ) 8.0 Hz, 4H, Ar-H), 7.67 (s, 1H, Ar-H),
7.36 (s, 1H, Ar-H), 7.20 (s, 1H, Ar-H), 6.69 (s, 1H, Ar-H),
3.88 (s, 3H, N-CH3), 3.46 (s, 3H, N-CH3), 3.52-3.84 (m,
6H, 3 × CH2), 2.76 (t, J ) 5.6 Hz, 2H, CH2), 2.72-2.68
(m, 4H, 2 × CH2), 1.86-1.80 (m, 4H, 2 × CH2). TLC (89:
10:1, CH2Cl2: MeOH: Et3N, Rf ) 0.50) with 68% yield. MS
calculated for C39H33F5N6O6 (M + H) 777.25, found 777.32.
Perfluorophenyl 1-Methyl-4-(4-(4-(1-methyl-5-(2-mor-
pholinoethylcarbamoyl)-1H-pyrrol-3-ylcarbamoyl)ben-
zoyl)benzamido)-1H-pyrrole-2-carboxylate (14{3}). 1H
NMR (400 MHz, CDCl3): δ 8.38 (s, 1H, NH), 8.16 (s, 1H,
NH), 7.99 (d, J ) 8.0 Hz, 2H, Ar-H), 7.95 (d, J ) 8.0 Hz,
2H, Ar-H), 7.84 (d, J ) 4.0 Hz, 2H, Ar-H), 7.83 (d, J ) 4.0
Hz, 2H, Ar-H), 7.77 (s, 1H, Ar-H), 7.29 (s, 1H, Ar-H), 7.21
(d, J ) 1.6 Hz, 1H, Ar-H), 6.66 (s, 1H, Ar-H), 3.97 (s, 3H,
N-CH3), 3.92 (s, 3H, N-CH3), 3.72 (t, J ) 4.4 Hz, 4H, 2
× CH2), 3.47 (q, J ) 5.6 Hz, 2H, CH2), 2.57 (t, J ) 5.6 Hz,
2H, CH2), 2.54-2.47 (m, 4H, 2 × CH2). TLC (94:5:1,
CH2Cl2:MeOH:Et3N, Rf ) 0.60) with 75% yield. MS
calculated for C39H33F5N6O7 (M + H) 793.24, found 793.31.
Perfluorophenyl 1-Methyl-4-(4-(4-(1-methyl-5-(3-mor-
pholinopropylcarbamoyl)-1H-pyrrol-3-ylcarbamoyl)ben-
zoyl)benzamido)-1H-pyrrole-2-carboxylate (14{4}). 1H
NMR (400 MHz, CDCl3): δ 9.36 (s, 1H, NH), 9.06 (s, 1H,
NH), 7.89 (d, J ) 8.0 Hz, 2H, Ar-H), 7.81 (d, J ) 8.0 Hz,
2H, Ar-H), 7.76 (d, J ) 1.6 Hz, 1H, Ar-H), 7.61 (t, J ) 8.4
Hz, 2H, Ar-H), 7.59 (d, J ) 8.0 Hz, 2H, Ar-H), 7.43 (t, J )
4.8 Hz, 1H, NH), 7.29 (d, J ) 1.6 Hz, 1H, Ar-H), 7.22 (d,
J ) 1.6 Hz, 1H, Ar-H), 6.83 (d, J ) 1.6 Hz, 1H, Ar-H),
3.91 (s, 3H, N-CH3), 3.81 (s, 3H, N-CH3), 3.71 (t, J )
4.0 Hz, 4H, 2 × CH2), 3.41 (q, J ) 5.6 Hz, 2H, CH2),
2.51-2.48 (m, 6H, 3 × CH2), 1.75-1.70 (m, 2H, CH2). TLC
(94:5:1, CH2Cl2:MeOH:Et3N, Rf ) 0.50) with 60% yield.
MS calculated for C40H35F5N6O7 (M + H) 807.26, found
807.32.
Perfluorophenyl 4-(4-(4-(5-(Cyclopropylmethylcarbam-
oyl)-1-methyl-1H-pyrrol-3-ylcarbamoyl)benzoyl)benza-
mido)-1-methyl-1H-pyrrole-2-carboxylate (14{5}). 1H NMR
(400 MHz, CDCl3): δ 8.57 (s, 1H, NH), 8.25 (s, 1H, NH),
7.94 (d, J ) 8.8 Hz, 2H, Ar-H), 7.89 (d, J ) 8.8 Hz, 2H,
Ar-H), 7.77 (d, J ) 8.4 Hz, 4H, Ar-H), 7.22 (d, J ) 1.6 Hz,
1H, Ar-H), 7.19 (d, J ) 1.6 Hz, 2H, Ar-H), 6.73 (d, J ) 1.6
Hz, 1H, Ar-H), 6.05 (t, J ) 4.8 Hz, 1H, Ar-H), 3.95 (s, 3H,
N-CH3), 3.87 (s, 3H, N-CH3), 3.21 (t, J ) 6.4 Hz. 2H,
CH2), 1.06-0.96 (m, 1H, CH), 0.52 (q, J ) 6.4 Hz, 2H,
CH2), 0.22 (q, J ) 5.2 Hz, 2H, CH2). TLC (95:5, CH2Cl2:
MeOH, Rf ) 0.40) with 68% yield. MS calculated for
C37H28F5N5O6 (M + H) 734.21, found 734.14.
7.24 (s, 1H, Ar-H), 7.17 (s, 1H, Ar-H), 6.72 (s, 1H, Ar-H),
3.91 (s, 3H, N-CH3), 3.80 (s, 3H, N-CH3), 3.40 (q, J )
4.8 Hz, 2H, CH2), 2.57-2.52 (m, 6H, 3 × CH2), 1.67 (t, J
) 6.0 Hz, 2H, CH2), 0.99 (t, J ) 7.6 Hz, 6H, 2 × CH3).
TLC (89:10:1, CH2Cl2: MeOH: Et3N, Rf ) 0.45) with 59%
yield. MS calculated for C40H37F5N6O6 (M + H) 793.28,
found 793.32.
Perfluorophenyl 4-(4-(4-(5-(2,5-Difluorobenzylcarbam-
oyl)-1-methyl-1H-pyrrol-3-ylcarbamoyl)benzoyl)benza-
mido)-1-methyl-1H-pyrrole-2-carboxylate (14{7}). 1H NMR
(400 MHz, DMSO-d6): δ 10.72 (s, 1H, NH), 10.53 (s, 1H,
NH), 8.61 (t, J ) 5.6 Hz, 1H, NH), 8.11 (d, J ) 7.2 Hz, 4H,
Ar-H), 8.09 (d, J ) 7.2 Hz, 2H, Ar-H), 7.89 (d, J ) 8.0 Hz,
4H, Ar-H), 7.87 (d, J ) 7.2 Hz, 2H, Ar-H), 7.81 (s, 1H,
Ar-H), 7.40-7.32 (m, 3H, Ar-H), 7.23-7.17 (m, 1H, Ar-
H), 7.10-7.01 (m, 2H, Ar-H), 4.38 (d, J ) 6.0 Hz, 2H, CH2),
3.91 (s, 3H, N-CH3), 3.81 (s, 3H, N-CH3). TLC (3:1, ethyl
acetate:hexane, Rf ) 0.60) with 71% yield. MS calculated
for C40H26F7N5O6 (M + H) 806.19, found 806.30.
Perfluorophenyl 1-Methyl-4-(4-(4-(1-methyl-5-(pyridin-
2-ylmethylcarbamoyl)-1H-pyrrol-3-ylcarbamoyl)benzoyl)-
1
benzamido)-1H-pyrrole-2-carboxylate (14{8}). H NMR
(400 MHz, CDCl3): δ 9.43 (s, 1H, NH), 9.22 (s, 1H, NH),
8.39 (d, J ) 5.2 Hz, 1H, Ar-H), 7.86 (d, J ) 8.4 Hz, 2H,
Ar-H), 7.81 (d, J ) 8.0 Hz, 2H, Ar-H), 7.73 (d, J ) 2.4 Hz,
1H, Ar-H), 7.6-7.55 (m, 4H, Ar-H), 7.31 (t, J ) 4.8 Hz,
1H, NH), 7.28-7.24 (m, 2H, Ar-H), 7.22 (s, 1H, Ar-H), 7.20
(s, 1H, Ar-H), 7.12-7.09 (m, 1H, Ar-H), 6.78 (s, 1H, Ar-
H), 4.56 (d, J ) 4.8 Hz, 2H, CH2), 3.88 (s, 3H, N-CH3),
3.76 (s, 3H, N-CH3). TLC (90:10, CH2Cl2:MeOH, Rf )
0.50) with 65% yield. MS calculated for C39H27F5N6O6 (M
+ H) 771.20, found 771.30.
Perfluorophenyl 1-Methyl-4-(4-(4-(1-methyl-5-(2-(py-
ridin-4-yl)ethylcarbamoyl)-1H-pyrrol-3-ylcarbamoyl)ben-
zoyl)benzamido)-1H-pyrrole-2-carboxylate (14{9}). 1H
NMR (400 MHz, CDCl3 and CD3OD): δ 9.71 (s, 1H, NH),
9.41 (s, 1H, NH), 8.31 (s, 2H, NH), 7.84 (d, J ) 8.8 Hz,
2H, Ar-H), 7.72 (d, J ) 8.0 Hz, 2H, Ar-H), 7.54 (d, J ) 8.4
Hz, 2H, Ar-H), 7.49 (d, J ) 8.0 Hz, 2H, Ar-H), 7.25 (d, J
) 1.6 Hz, 1H, Ar-H), 7.23 (s, 1H, Ar-H), 7.04 (s, 2H, Ar-
H), 6.63 (s, 1H, Ar-H), 6.58 (t, J ) 4.8 Hz, 1H, NH), 3.88
(s, 3H, N-CH3), 3.77 (s, 3H, N-CH3), 3.55 (q, J ) 5.6 Hz,
2H, CH2), 2.81 (t, J ) 6.4 Hz, 2H, CH2). TLC (90:10,
CH2Cl2:MeOH, Rf ) 0.50) with 55% yield. MS calculated
for C40H29F5N6O6 (M + H) 785.22, found 785.35.
Perfluorophenyl 1-Methyl-4-(4-(4-(1-methyl-5-(3-(pyrro-
lidin-1-yl)propylcarbamoyl)-1H-pyrrol-3-ylcarbamoyl)ben-
zoyl)benzamido)-1H-pyrrole-2-carboxylate (14{10}). 1H NMR
(400 MHz, CDCl3): δ 9.40 (s, 1H, NH), 8.92 (s, 1H, NH),
7.92 (s, 1H, Ar-H), 7.90 (d, J ) 7.2 Hz, 2H, Ar-H), 7.81 (d,
J ) 7.2 Hz, 2H, Ar-H), 7.62 (d, J ) 5.2 Hz, 4H, Ar-H),
7.61 (d, J ) 4.8 Hz, 2H, Ar-H), 7.29 (s, 1H, Ar-H), 7.19 (s,
1H, Ar-H), 6.65 (s, 1H, Ar-H), 3.91 (s, 3H, N-CH3), 3.80
(s, 3H, N-CH3), 3.44-3.38 (m, 2H, CH2), 2.60 (t, J ) 5.6
Hz, 2H, CH2), 2.53-2.46 (m, 4H, 2 × CH2), 1.81-1.74 (m,
4H, 2 × CH2), 1.70 (t, J ) 5.6 Hz, 2H, CH2). TLC (89:10:
1, CH2Cl2:MeOH:Et3N, Rf ) 0.40) with 76% yield. MS
calculated for C40H35F5N6O6 (M + H) 791.26, found 791.35.
Perfluorophenyl 4-(4-(4-(5-(3-(Diethylamino)Propylcar-
bamoyl)-1-methyl-1H-pyrrol-3-ylcarbamoyl)benzoyl)ben-
1
zamido)-1-methyl-1H-pyrrole-2-carboxylate (14{6}). H
NMR (400 MHz, CDCl3): δ 9.55 (s, 1H, NH), 9.15 (s, 1H,
NH), 8.11 (t, J ) 4.8 Hz, 1H, NH), 7.90 (d, J ) 8.0 Hz, 2H,
Ar-H), 7.81 (d, J ) 8.8 Hz, 2H, Ar-H), 7.75 (s, 1H, Ar-H),
7.61-7.57 (m, 5H, Ar-H), 7.32 (d, J ) 1.6 Hz, 1H, Ar-H),