# Synthesis of Novel Symmetrical and Unsymmetrical o-Phthalic Acid Diamides

Authors: Padam Praveen Kumar; Yervala Dathu Reddy; Chittireddy Venkata Ramana Reddy; Bhoomireddy Rama Devi; Pramod Kumar Dubey
Journal: Organic Chemistry International
 (2014)

---

## Abstract

Phthalic anhydride was treated with secondary amines in acetic acid yielding 2-(diethyl (or) 4-alkylpiperazine or morpholine-1-carbonyl) benzoic acids. The latter were reacted, again, with secondary amines and arylamines by using the coupling reagent HATU and Et3N as a base in DMF giving the novel symmetrical o-phthalic acid diamides [
o-R
1
R
1
NCOC
6
H
4
CONR
1
R
1
],  unsymmetrical o-phthalic acid diamides [
o-R
1
R
1
NCOC
6
H
4
CONR
1
R
2
], and primary amidic-secondary amidic containing unsymmetrical o-phthalic acid diamides [
o-R
1
R
1
NCOC
6
H
4
CONHAr
], respectively.


---

## Body

## 1. Introduction

Phthalic anhydride is used in the manufacture of dialkylphthalates [1, 2] which find application as plasticisers for polymers like polyvinyl chloride (PVC) and polyvinylacetate (PVA). It is used in the manufacture of phenolphthalein indicator [3, 4], anthraquinone [5] (a versatile, raw materials in the dye industry [6]), and metal phthalocyanines [7]. Phthalocyanine compounds are used in a variety of applications [7] in addition to their use as pigments, in paints [8] and in many types of dyestuffs [7]. Phthalic anhydride derivatives have been widely reported to possess beneficial pharmaceutical effects, like analgesic [9], anti-inflammatory [10] and antiviral effects [11].Dunlap and Cummer reported [12] the preparation of symmetrical o-phthalic acid diamides [o-ArNHCOC6H4CONHAr] by the reaction of phthaloyl dichloride with two moles of aniline in ether at RT. Dann et al. reported [13] the preparation of symmetrical o-phthalic acid diamides by the reaction of phthaloyl dichloride with two moles of aniline in the presence of sodium fluoride in benzene under reflux for 1 h. de Toranzo and Brieux reported [14] the synthesis of unsymmetrical diamides [ArNHCOC6H4CONHAr1] by the reaction of phthalphenylisoimide with anilines in ether at RT. Reynolds reported [15] that unsymmetrical diamides [ArNHCOC6H4CONHAr1] can be made by the reaction of N-arylphthalamic acid with the sodium salt of o- or p-methylaniline in an atmosphere of nitrogen for 1 h at 75°C. However, these methods suffer from drawbacks such as long reaction times, excess use of organic solvents, harsh refluxing conditions, and preparation of difficult starting materials from phthalic anhydride by the reaction with primary amines in the presence of trifluoroacetic anhydride. Keeping these facts in mind, we wish to report our results on reactions of phthalic anhydride with primary and secondary amines using HATU as a coupling reagent. Probably, this appears to be the first ever case of facile preparation of symmetrical and unsymmetrical o-phthalic acid diamides. The use of HATU as a coupling agent has been reported in the literature for reactions such as amide bond formation in solid phase synthesis [16–18] and peptides synthesis [19]. However, its use in the preparation of diamides from phthalic anhydride with amines has probably not been reported so far.


## 2. Results and Discussion

Phthalic anhydride1 was treated with the secondary amines2a–2e in acetic acid at RT for 10–15 min resulting in the formation of 2-(diethyl (or) 4-alkylpiperazine (or) morpholine-1-carbonyl)benzoic acid3a–3e. Reaction of3a with the piperazine2b in the presence of o-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluroniumhexafluorophosphate (HATU) and Et3N at 0–5°C for 40–45 min in DMF gave5a. Alternatively, this compound was prepared by treating 2-(piperazine-1-carbonyl)benzoic acid3bwithdiethylamine2a by HATU and Et3N at 0–5°C for 40–45 min in DMF to form N,N-diethyl-2-(piperazine-1-carbonyl)benzamide5a. This reaction was examined by carrying out the condensation of 2-(diethylcarbonyl)benzoic acid3a (1 mmol) with piperazine2b (1 mmol) in the presence different coupling reagents (HATU, EDC.HCl/HOBt (1-hydroxybenzotriazole), DCC (N,N′-dicyclohexylcarbodiimide), HBTU and PTSA (4-methylbenzenesulfonic acid)) and tertiary bases (Et3N and DBU (2, 3, 4, 6, 7, 8, 9, 10-octahydropyrimido [
1
,
2-a
] azepine) at different temperatures in DMF as a solvent (Table 1) with a view to study the generalisation of condensation between3 and2. However, coupling of3a with2b in the presence of HATU and Et3N at 0–5°C for 40–45 min in DMF was found to be the best method giving5a in quality and yield (≥80%) (Table 1, entry1).Table 1
Effect of coupling reagent, tertiary base, and temperature on condensation of3a with 2b in DMF yielding 5a.
Entry
Coupling reagent
Tertiary base
Temp./°C
Time/min
5a (%)
1
HATU
E
t
3
N
0–5
40–45
80
2
HATU
Et3N
RT
40–45
78
3
HATU
DBU
0–5
55–65
70
4
HATU
DBU
RT
50–55
70
5
HATU
Et3N
50–60
35–40
73
6
DCC
—
0–5
120–130
45
7
DCC
—
RT
100–110
48
8
DCC/HOBt
—
0–5
110–120
50
9
DCC/HOBt
—
RT
100–110
50
10
DCC/HOBt
—
50–60
55–60
72
11
EDC·HCl/HOBt
Et3N
0–5
80–85
70
12
EDC·HCl/HOBt
Et3N
RT
70–80
70
13
EDC·HCl/HOBt
DBU
0–5
70–80
60
14
EDC·HCl/HOBt
DBU
RT
70–75
65
15
EDC·HCl/HOBt
Et3N
50–60
65–70
72
16
HBTU
Et3N
0–5
70–75
70
17
HBTU
Et3N
RT
65–70
70
18
HBTU
DBU
0–5
70–80
65
19
HBTU
DBU
RT
65–75
65
20
HBTU
Et3N
50–60
50–55
70
21
PTSA
—
0–5
120–125
—
22
PTSA
—
RT
120–125
—
23
PPA
—
100
60–65
40Using the above-stated optimised conditions,3a–3e were condensed into2a–2e using HATU and Et3N at 0–5°C for 40–65 min in DMF yielding4a–4e and5a–5j (Scheme 1) (Tables 2 and 3) in excellent yield. The structures of the products have been established on the basis of their spectral and analytical data. (Please see experimental section)Table 2
Characterization data, reaction time, and yields of3a–3e obtained 1 and 2a–2e.
Entry
Starting material used
Product obtained
Time (min)
Yield≠
M.P (°C)
1
2a
3a
10–12
85
145–148
2
2b
3b
12–15
85
>220
3
2c
3c
15–18
83
>220
4
2d
3d
15–18
80
>220
5
2e
3e
15–20
81
>220
≠Refers to yields of crude products only.Table 3
Characterization data, reaction time, and yields of4a–4e and 5a–5j obtained from 3a–3e and 2a–2e.
Entry
Starting material used
Product obtained
Time (min)
Yield≠
M.P (°C)
1
3a
2a
4a
40–45
85
>220
2
3b
2b
4b
40–45
85
>220
3
3c
2c
4c
50–55
80
>220
4
3d
2d
4d
50–55
80
>220
5
3e
2e
4e
40–45
80
>220
6
3a
2b
5a
40–45
85
>220
7
3a
2c
5b
50–55
81
110–112
8
3a
2d
5c
50–55
84
115–118
9
3a
2e
5d
50–55
85
80–82
10
3b
2a
5a
40–45
83
>220
11
3b
2c
5e
50–55
84
>220
12
3b
2d
5f
50–55
85
>220
13
3b
2e
5g
60–65
85
85–87
14
3c
2a
5b
60–65
81
110–112
15
3c
2b
5e
50–55
83
>220
16
3c
2d
5h
50–55
85
>220
17
3c
2e
5i
50–55
85
90–92
18
3d
2a
5c
60–65
80
115–118
19
3d
2b
5f
50–55
80
>220
20
3d
2c
5h
40–45
85
>220
21
3d
2e
5j
40–45
83
>220
22
3e
2a
5d
40–45
80
80–82
23
3e
2b
5g
50–55
84
85–87
24
3e
2c
5i
50–55
84
90–92
25
3e
2d
5j
40–45
83
>220
≠Refers to yields of crude products only.Scheme 1
Synthetic routes to4a–4e and5a–5j.Condensation of3a–3ewith arylamines6a–6e in the presence of HATU and Et3N at 0–5°C for 40–55 min in DMF gave primary amidic-secondary amidic containing unsymmetrical o-phthalic acid diamides [o-R1R1NCOC6H4CONHAr]7a–7y (Scheme 2) (Table 4). The structures of the products have been established on the basis of their spectral and analytical data. An alternate protocol was attemptedto synthesize7a–7y by treatment of1with aniline6a in acetic acid at 0–5°C for 10–15 min which gave 2-(phenylcarbamoyl)benzoic acid8a
18 and subsequent reaction of8a with diethylamine2ain the presence of HATU and Et3N at RT for 20–25 min in DMF which resulted in the formation of 2-phenylisoindoline-1, 3-dione9a
18.Table 4
Characterization data reaction time and yield of7a–7y obtained from 3a–3e and 6a–6e.
Entry
Starting material used
Product obtained
Time (min)
Yield≠
M.P (°C)
1
3a
6a
7a
40–45
85
115–118
2
3b
6a
7b
50–55
82
120–123
3
3c
6a
7c
40–45
84
123–125
4
3d
6a
7d
50–55
85
>220
5
3e
6a
7e
50–55
80
126–128
6
3a
6b
7f
40–45
83
128–130
7
3b
6b
7g
40–45
82
138–140
8
3c
6b
7h
50–55
82
120–123
9
3d
6b
7i
50–55
85
>220
10
3e
6b
7j
40–45
80
122–124
11
3a
6c
7k
50–55
82
120–124
12
3b
6c
7l
40–45
85
130–132
13
3c
6c
7m
50–55
85
170–174
14
3d
6c
7n
50–55
80
>220
15
3e
6c
7o
40–45
80
140–143
16
3a
6d
7p
40–45
80
125–128
17
3b
6d
7q
50–55
82
135–137
18
3c
6d
7r
50–55
82
180–183
19
3d
6d
7s
40–45
80
>220
20
3e
6d
7t
40–45
85
142–145
21
3a
6e
7u
40–45
84
128–130
22
3b
6e
7v
40–45
85
133–135
23
3c
6e
7w
50–55
80
190–192
24
3d
6e
7x
50–55
82
>220
25
3e
6e
7y
40–45
84
145–148
≠Refers to yields of crude products only.Scheme 2
Synthetic routes to7a–7y.


## 3. Conclusion

In conclusion, we have developed novel syntheses of symmetrical4a–4e and unsymmetrical5a–5j and7a–7y o-phthalic acid diamides. This approach presents a simple and useful synthetic process which requires a few minutes of reaction time, easily available starting materials and straight forward and easy workup procedure. Probably, this appears to be the first ever case of facile preparation of symmetrical and unsymmetrical o-phthalic acid diamides. The use of HATU as a coupling agent has been reported in the literature for reactions such as amide bond formation in solid phase synthesis and peptides synthesis. However, its use in the preparation of diamides from phthalic anhydride with amines has probably not been reported so far. The overall yields of these compounds are very good.


## 4. Materials and Methods

Melting points are uncorrected and were determined in open capillary tubes in sulphuric acid bath, TLC was run on silica gel-G, visualization was done using iodine or UV light, and IR spectra were recorded using PerkinElmer 1000 instrument in KBr pellets. 1HNMR spectra were recorded in DMSO-d6 using TMS as internal standard using 400 MHz spectrometer. Mass spectra were recorded on Agilent-LCMS instrument under CI conditions and given by Q
+
1 values only. Starting1,2, and6 were obtained from commercial sources and used as such.


### 4.1. Preparation of3a–3e

A mixture of1a(10 mM),2a–2e(10 Mm) and CH3COOH (20 mL) was stirred at RT for 10–20 min. A colourless solid separated out from reaction mixture which was filtered, washed with hexane (10 mL), and dried. The crude product was recrystallized from suitable solvent to obtain3a–3e.


### 4.2. Preparation of4a–4e &5a–5j

A mixture of3a–3e (10 mM),2a–2e(10 mM) HATU (10 mM), Et3N (10 mM), and DMF (15 mL) was stirred at 0–5°C for 40–65 min. Then, ice-cold water (50 mL) was added to the reaction mixture. The separated solid was filtered, washed with water (10 mL), and dried. The product was recrystallized from a suitable solvent to obtain4a–4e and5a–5j.


### 4.3. Preparation of7a–7y

A mixture of3a–3e (10 mM),6a–6e(10 mM), HATU (10 mM), Et3N (10 mM), and DMF (15 mL) was stirred at 0–5°C for 40–55 min. Then, ice-cold water (50 mL) was added to the reaction mixture. The separated solid was filtered, washed with water (10 mL), and dried. The product was recrystallized from a suitable solvent to obtain7a–7y.


## 4.1. Preparation of3a–3e

A mixture of1a(10 mM),2a–2e(10 Mm) and CH3COOH (20 mL) was stirred at RT for 10–20 min. A colourless solid separated out from reaction mixture which was filtered, washed with hexane (10 mL), and dried. The crude product was recrystallized from suitable solvent to obtain3a–3e.


## 4.2. Preparation of4a–4e &5a–5j

A mixture of3a–3e (10 mM),2a–2e(10 mM) HATU (10 mM), Et3N (10 mM), and DMF (15 mL) was stirred at 0–5°C for 40–65 min. Then, ice-cold water (50 mL) was added to the reaction mixture. The separated solid was filtered, washed with water (10 mL), and dried. The product was recrystallized from a suitable solvent to obtain4a–4e and5a–5j.


## 4.3. Preparation of7a–7y

A mixture of3a–3e (10 mM),6a–6e(10 mM), HATU (10 mM), Et3N (10 mM), and DMF (15 mL) was stirred at 0–5°C for 40–55 min. Then, ice-cold water (50 mL) was added to the reaction mixture. The separated solid was filtered, washed with water (10 mL), and dried. The product was recrystallized from a suitable solvent to obtain7a–7y.


## 5. Supporting Information

3a: IR (KBr): 3100–3400 cm
-
1 (broad medium, –NH and –OH groups put together), 1720 cm
-
1 (sharp, strong, –CO– of acid group), 1655 cm
-
1 (sharp, storng, –CO– of amide group); 1H-NMR: δ 0.8 (t, 3H, –CH3), δ 1.2 (t, 3H, –CH3), δ 3.0 (q, 2H, –CH2), δ 3.6 (q, 2H, –CH2), 7.0–8.0 (m, 4H, Ar-H), 13.00 (s, 1H, –COOH, D2O exchangeable), 10.12 (s, 1H, –NH, D2O exchangeable). 13C NMR (DMSO-d6, 400 MHz): 12.3, 41.4, 123.1, 128.5, 129.3, 129.5, 160.2, 165.5. Ms: m
/
z = 222 (M+. + 1).3b: IR (KBr): 3100–3400 cm
-
1 (broad medium, –NH and –OH groups put together), 1725 cm
-
1 (sharp, strong, –CO– of acid group), 1670 cm
-
1 (sharp, storng, –CO– of amide group); 1H-NMR: δ 2.2 (s, 1H, –NH), δ 3.0 (t, 2H, –CH2), δ 3.2 (t, 2H, –CH2), δ 3.4 (t, 2H, –CH2), δ 3.8 (t, 2H, –CH2), 7.0–8.0 (m, 4H, Ar-H), 13.00 (s, 1H, –COOH, D2O exchangeable). 13C NMR (DMSO-d6, 400 MHz): 49.4, 50.1, 51.4, 51.9, 124.1, 125.5, 127.3, 128.5, 161.2, 164.8. Ms: m
/
z = 235 (M+. + 1).3c: IR (KBr): 3100–3400 cm
-
1 (broad medium, –NH and –OH groups put together), 1730 cm
-
1 (sharp, strong, –CO– of acid group), 1655 cm
-
1 (sharp, storng, –CO– of amide group); 1H-NMR: δ 1.2 (t, 3H, –CH3), δ 2.6 (q, 2H, –CH2), δ 3.0 (t, 2H, –CH2), δ 3.2 (t, 2H, –CH2), δ 3.4 (t, 2H, –CH2), δ 3.8 (t, 2H, –CH2), 7.0–8.0 (m, 4H, Ar-H), 13.2 (s, 1H, –COOH, D2O exchangeable). 13C NMR (DMSO-d6, 400 MHz): 12.5, 49.4, 50.1, 50.9, 51.9, 52.2, 123.1, 124.5, 125.3, 127.5, 163.2, 164.8. Ms: m
/
z = 263 (M+. + 1).3d: IR (KBr): 3100–3400 cm
-
1 (broad medium, –NH and –OH groups put together), 1720 cm
-
1 (sharp, strong, –CO– of acid group), 1660 cm
-
1 (sharp, storng, –CO– of amide group); 1H-NMR: δ 1.6 (t, 3H, –CH3), δ 3.0 (t, 2H, –CH2), δ 3.2 (t, 2H, –CH2), δ 3.4 (t, 2H, –CH2), δ 3.8 (t, 2H, –CH2), 7.0–8.0 (m, 4H, Ar-H), 13.1 (s, 1H, –COOH, D2O exchangeable). 13C NMR (DMSO-d6, 400 MHz): 39.4, 55.1, 55.9, 55.9, 55.2, 126.1, 127.5, 128.3, 129.5, 160.2, 165.8. Ms: m
/
z = 249 (M+. + 1).3e: IR (KBr): 3100–3400 cm
-
1 (broad medium, –NH and –OH groups put together), 1720 cm
-
1 (sharp, strong, –CO– of acid group), 1655 cm
-
1 (sharp, storng, –CO– of amide group); 1H-NMR: δ 3.0 (t, 2H, –CH2), δ 3.2 (t, 2H, –CH2), δ 3.4 (t, 2H, –CH2), δ 3.8 (t, 2H, –CH2), 7.0–8.0 (m, 4H, Ar-H), 13.1 (s, 1H, –COOH, D2O exchangeable). 13C NMR (DMSO-d6, 400 MHz): 50.2, 50.6, 71.9, 72.2, 125.1, 125.5, 126.3, 127.5, 162.2, 164.8. Ms: m
/
z = 236 (M+. + 1).4a: IR (KBr): 3100–3400 cm
-
1 (broad medium, –NH–), 1680 cm
-
1 (sharp, strong, –CO– of amide group), 1665 cm
-
1 (sharp, strong, –CO– of amide group); 1H-NMR: δ 1.2 (t, 6H, –CH3, –CH3), δ 1.4 (t, 6H, –CH3, –CH3), δ 2.8 (q, 4H, –CH2, –CH2) δ 3.2 (q, 4H, –CH2, –CH2), 7.0–8.0 (m, 4H, Ar-H). 13C NMR (DMSO-d6, 400 MHz): 12.9, 14.1, 31.6, 36.7, 39.1, 43.5, 125.3, 126.5, 127.1, 129.3, 163.6, 169.6. Ms: m
/
z = 277 (M+. + 1).4b: IR (KBr): 3100–3400 cm
-
1 (broad medium, –NH–), 1685 cm
-
1 (sharp, strong, –CO– of amide group), 1665 cm
-
1 (sharp, strong, –CO– of amide group); 1H-NMR: δ 2.2 (s, 2H, –NH, –NH), δ 3.0 (t, 8H, Four –CH2 groups), δ 3.4 (t, 8H, Four –CH2 groups), 7.0–8.0 (m, 4H, Ar-H). 13C NMR (DMSO-d6, 400 MHz): 47.4, 48.6, 49.7, 50.9, 51.5, 52.4, 125.3, 125.5, 127.1, 128.6, 164.3, 167.6. Ms: m
/
z = 303 (M+. + 1).4c: IR (KBr): 3100–3400 cm
-
1 (broad medium, –NH–), 1660 cm
-
1 (sharp, strong, –CO– of amide group), 1665 cm
-
1 (sharp, strong, –CO– of amide group); 1H-NMR: δ 1.3 (t, 6H, –CH3, –CH3), δ 2.8 (q, 4H, –CH2, –CH2), δ 3.2 (t, 8H, Four –CH2 groups), δ 3.2 (t, 8H, Four –CH2 groups), 7.0–8.0 (m, 4H, Ar-H). 13C NMR (DMSO-d6, 400 MHz): 12.3, 16.1, 46.4, 47.6, 48.7, 49.1, 50.5, 51.4, 123.3, 124.5, 128.1, 128.9, 164.6, 168.6. Ms: m
/
z = 359 (M+. + 1).4d: IR (KBr): 3100–3400 cm
-
1 (broad medium, –NH–), 1670 cm
-
1 (sharp, strong, –CO– of amide group), 1665 cm
-
1 (sharp, strong, –CO– of amide group); 1H-NMR: δ 1.4 (t, 6H, –CH3, –CH3), δ 3.0 (t, 8H, Four –CH2 groups), δ 3.2 (t, 8H, Four –CH2 groups), 7.0–8.0 (m, 4H, Ar-H). 13C NMR (DMSO-d6, 400 MHz): 32.3, 33.4, 48.4, 48.9, 49.7, 50.5, 52.4, 55.3, 125.3, 125.6, 128.3, 129.9, 165.2, 169.3. Ms: m
/
z = 331 (M+. + 1).4e: IR (KBr): 3100–3400 cm
-
1 (broad medium, –NH–), 1675 cm
-
1 (sharp, strong, –CO– of amide group), 1665 cm
-
1 (sharp, strong, –CO– of amide group); 1H-NMR: δ 3.0 (t, 8H, Four –CH2 groups), δ 3.2 (t, 8H, Four –CH2 groups), 7.0–8.0 (m, 4H, Ar-H). 13C NMR (DMSO-d6, 400 MHz): 49.3, 49.9, 50.7, 52.8, 55.9, 56.8, 125.4, 126.3, 127.4, 128.9, 164.2, 167.3. Ms: m
/
z = 305 (M+. + 1).5a: IR (KBr): 3100–3400 cm
-
1 (broad medium, –NH–), 1690 cm
-
1 (sharp, strong, –CO– of amide group), 1660 cm
-
1 (sharp, strong, –CO– of amide group); 1H-NMR: δ 1.0–1.2 (t, 6H, –CH3, –CH3), δ 2.2 (s, 1H, –NH), δ 3.0 (t, 4H, –CH2, –CH2), δ 3.2 (t, 4H, –CH2, –CH2), δ 3.4 (q, 2H, –CH2), δ 3.6 (q, 2H, –CH2, –CH2), 7.0–8.0 (m, 4H, Ar-H). 13C NMR (DMSO-d6, 400 MHz): 12.9, 31.7, 43.5, 44.6, 51.1, 52.5, 123.1, 124.3, 128.3, 129.6, 161.7, 165.5. Ms: m
/
z = 290 (M+. + 1).5b: IR (KBr): 3100–3400 cm
-
1 (broad medium, –NH–), 1680 cm
-
1 (sharp, strong, –CO– of amide group), 1650 cm
-
1 (sharp, strong, –CO– of amide group); 1H-NMR: δ 1.0–1.2 (t, 6H, –CH3, –CH3), δ 1.4 (t, 3H, –CH3), δ 2.2 (q, 2H, –CH2), δ 3.0 (t, 4H, –CH2, –CH2), δ 3.2 (t, 4H, –CH2, –CH2), δ 3.4 (q, 2H, –CH2), δ 3.6 (q, 2H, –CH2, –CH2), 7.0–8.0 (m, 4H, Ar-H). 13C NMR (DMSO-d6, 400 MHz): 12.9, 13.6, 31.5, 44.5, 45.6, 48.6, 54.1, 55.5, 123.6, 125.3, 128.3, 129.6, 162.7, 165.4. Ms: m
/
z = 318 (M+. + 1).5c: IR (KBr): 3100–3400 cm
-
1 (broad medium, –NH–), 1695 cm
-
1 (sharp, strong, –CO– of amide group), 1655 cm
-
1 (sharp, strong, –CO– of amide group); 1H-NMR: δ 1.0–1.2 (t, 6H, –CH3, –CH3), δ 1.8 (t, 3H, –CH3), δ 3.0 (t, 4H, –CH2, –CH2), δ 3.2 (t, 4H, –CH2, –CH2), δ 3.4 (q, 2H, –CH2), δ 3.6 (q, 2H, –CH2, –CH2), 7.0–8.0 (m, 4H, Ar-H). 13C NMR (DMSO-d6, 400 MHz): 13.9, 32.7, 41.5, 44.6, 45.5, 53.1, 54.5, 122.3, 125.3, 129.2, 129.9, 164.7, 166.4. Ms: m
/
z = 304 (M+. + 1).5d: IR (KBr): 3100–3400 cm
-
1 (broad medium, –NH–), 1680 cm
-
1 (sharp, strong, –CO– of amide group), 1655 cm
-
1 (sharp, strong, –CO– of amide group); 1H-NMR: δ 1.0–1.2 (t, 6H, –CH3, –CH3), δ 3.0 (t, 4H, –CH2, –CH2), δ 3.2 (t, 4H, –CH2, –CH2), δ 3.4 (q, 2H, –CH2), δ 3.6 (q, 2H, –CH2, –CH2), 7.0–8.0 (m, 4H, Ar-H). 13C NMR (DMSO-d6, 400 MHz): 13.2, 33.4, 44.3, 45.2, 50.1, 52.4, 124.2, 123.5, 125.4, 125.7, 160.3, 165.6. Ms: m
/
z = 291 (M+. + 1).5e: IR (KBr): 3100–3400 cm
-
1 (broad medium, –NH–), 1690 cm
-
1 (sharp, strong, –CO– of amide group), 1665 cm
-
1 (sharp, strong, –CO– of amide group); 1H-NMR: δ 1.4 (t, 3H, –CH3), δ 2.2 (q, 2H, –CH2), δ 2.2 (s, 1H, –NH), δ 2.8–3.6 (t, 16H, eight –CH2 groups), 7.0–8.0 (m, 4H, Ar-H). 13C NMR (DMSO-d6, 400 MHz): 12.4, 29.4, 30.2, 31.7, 33.4, 34.3, 42.5, 43.6, 50.2, 51.2, 124.1, 125.2, 127.3, 129.3, 160.3, 164.2. Ms: m
/
z = 331 (M+. + 1).5f: IR (KBr): 3100–3400 cm
-
1 (broad medium, –NH–), 1690 cm
-
1 (sharp, strong, –CO– of amide group), 1650 cm
-
1 (sharp, strong, –CO– of amide group); 1H-NMR: δ 1.6 (t, 3H, –CH3), δ 2.2 (s, 1H, –NH), δ 2.8–3.6 (t, 16H, eight –CH2 groups), 7.0–8.0 (m, 4H, Ar-H). 13C NMR (DMSO-d6, 400 MHz): 28.4, 31.4, 32.5, 33.3, 35.4, 41.4, 42.4, 51.4, 52.3, 125.2, 126.1, 128.3, 129.2, 161.6, 165.1. Ms: m
/
z = 317 (M+. + 1).5g: IR (KBr): 3100–3400 cm
-
1 (broad medium, –NH–), 1680 cm
-
1 (sharp, strong, –CO– of amide group), 1655 cm
-
1 (sharp, strong, –CO– of amide group); 1H-NMR: δ 2.2 (s, 1H, –NH), δ 2.8–3.6 (t, 16H, eight –CH2 groups), 7.0–8.0 (m, 4H, Ar-H). 13C NMR (DMSO-d6, 400 MHz): 30.1, 31.3, 33.5, 34.2, 42.6, 43.8, 50.1, 51.4, 123.2, 125.1, 128.2, 129.3, 160.3, 165.3. Ms: m
/
z = 304 (M+. + 1).5h: IR (KBr): 3100–3400 cm
-
1 (broad medium, –NH–), 1690 cm
-
1 (sharp, strong, –CO– of amide group), 1655 cm
-
1 (sharp, strong, –CO– of amide group); 1H-NMR: δ 1.4 (t, 3H, –CH3), δ 1.8 (t, 3H, –CH3), δ 2.2 (q, 2H, –CH2), δ 2.8–3.6 (t, 16H, eight –CH2 groups), 7.0–8.0 (m, 4H, Ar-H). 13C NMR (DMSO-d6, 400 MHz): 13.2, 28.6, 29.5, 32.2, 33.7, 34.5, 35.4, 43.5, 44.5, 53.5, 54.6, 125.5, 126.4, 126.9, 129.5, 161.3, 165.9. Ms: m
/
z = 345 (M+. + 1).5i: IR (KBr): 3100–3400 cm
-
1 (broad medium, –NH–), 1680 cm
-
1 (sharp, strong, –CO– of amide group), 1650 cm
-
1 (sharp, strong, –CO– of amide group); 1H-NMR: δ 1.4 (t, 3H, –CH3), δ 2.2 (q, 2H, –CH2), δ 2.8–3.6 (t, 16H, eight –CH2 groups), 7.0–8.0 (m, 4H, Ar-H). 13C NMR (DMSO-d6, 400 MHz): 13.2, 29.4, 31.2, 32.2, 33.2, 34.5, 42.7, 44.8, 50.9, 51.9, 124.3, 125.9, 127.8, 129.0, 160.7, 168.9. Ms: m
/
z = 332 (M+. + 1).5j: IR (KBr): 3100–3400 cm
-
1 (broad medium, –NH–), 1670 cm
-
1 (sharp, strong, –CO– of amide group), 1655 cm
-
1 (sharp, strong, –CO– of amide group); 1H-NMR: δ 1.6 (t, 3H, –CH3), δ 2.8–3.6 (t, 16H, Eight –CH2 groups), 7.0–8.0 (m, 4H, Ar-H).13C NMR (DMSO-d6, 400 MHz): 28.4, 33.2, 34.7, 35.4, 39.3, 44.5, 47.6, 53.2, 55.2, 127.1, 128.2, 129.3, 129.9, 163.3, 169.4. Ms: m
/
z = 318 (M+. + 1).7a: IR (KBr): 3100–3400 cm
-
1 (broad medium, –NH–), 1680 cm
-
1 (sharp, strong, –CO– of acid group), 1645 cm
-
1 (sharp, strong, –CO– of amide group); 1H-NMR: δ 1.0 (t, 6H, –CH3, –CH3), δ 3.2 (q, 2H, –CH2), δ 3.4 (q, 2H, –CH2), 7.0–8.0 (m, 9H, Ar-H), 10.6 (s, 1H, –NH, D2O exchangeable). 13C NMR (DMSO-d6, 400 MHz): 12.2, 13.4, 37.9, 42.5, 123.4, 126.2, 127.8, 128.1, 128.5, 130.3, 134.1, 137.4, 139.1, 165.8, 169.2. Ms: m
/
z = 297 (M+. + 1).7b: IR (KBr): 3100–3400 cm
-
1 (broad medium, –NH–), 1680 cm
-
1 (sharp, strong, –CO– of acid group), 1645 cm
-
1 (sharp, strong, –CO– of amide group); 1H-NMR: δ 2.2 (s, 1H, –NH), δ 3.0 (t, 2H, –CH2), δ 3.2 (t, 2H, –CH2), δ 3.4 (t, 2H, –CH2), δ 3.8 (t, 2H, –CH2), 7.0–8.0 (m, 9H, Ar-H), 10.4 (s, 1H, –NH, D2O exchangeable).13C NMR (DMSO-d6, 400 MHz): 49.3, 50.3, 51.5, 51.3, 124.3, 124.5, 125.5, 126.4, 127.3, 128.5, 129.5, 129.9, 131.5, 163.2, 164.5. Ms: m
/
z = 310 (M+. + 1).7c: IR (KBr): 3100–3400 cm
-
1 (broad medium, –NH–), 1690 cm
-
1 (sharp, strong, –CO– of acid group), 1645 cm
-
1 (sharp, strong, –CO– of amide group); 1H-NMR: δ 1.2 (t, 3H, –CH3), δ 2.6 (q, 2H, –CH2), δ 3.0 (t, 2H, –CH2), δ 3.2 (t, 2H, –CH2), δ 3.4 (t, 2H, –CH2), δ 3.8 (t, 2H, –CH2), 7.0–8.0 (m, 9H, Ar-H), 10.4 (s, 1H, –NH, D2O exchangeable). 13C NMR (DMSO-d6, 400 MHz): 12.6, 44.5, 47.3, 48.5, 50.5, 51.3, 120.3, 122.7, 125.4, 126.3, 127.7, 128.3, 129.2, 130.9, 131.4, 160.6, 164.9. Ms: m
/
z = 338 (M+. + 1).7d: IR (KBr): 3100–3400 cm
-
1 (broad medium, –NH–), 1690 cm
-
1 (sharp, strong, –CO– of acid group), 1655 cm
-
1 (sharp, strong, –CO– of amide group); 1H-NMR: δ 1.6 (t, 3H, –CH3), δ 3.0 (t, 2H, –CH2), δ 3.2 (t, 2H, –CH2), δ 3.4 (t, 2H, –CH2), δ 3.8 (t, 2H, –CH2), 7.0–8.0 (m, 9H, Ar-H), 13.00 (s, 1H, –NH, D2O exchangeable). 13C NMR (DMSO-d6, 400 MHz): 34.5, 46.4, 47.2, 48.6, 50.2, 121.2, 123.4, 123.9, 124.6, 125.6, 126.3, 128.2, 131.9, 132.4, 164.2, 169.2. Ms: m
/
z = 324 (M+. + 1).7e: IR (KBr): 3100–3400 cm
-
1 (broad medium, –NH–), 1680 cm
-
1 (sharp, strong, –CO– of acid group), 1660 cm
-
1 (sharp, strong, –CO– of amide group); 1H-NMR: δ 3.0 (t, 2H, –CH2), δ 3.2 (t, 2H, –CH2), δ 3.4 (t, 2H, –CH2), δ 3.8 (t, 2H, –CH2), 7.0–8.0 (m, 8H, Ar-H), 13.00 (s, 1H, –NH, D2O exchangeable). 13C NMR (DMSO-d6, 400 MHz): 50.3, 51.3, 71.5, 72.3, 120.3, 121.2, 124.2, 125.6, 128.1, 128.9, 129.1, 129.9, 131.4, 165.1, 166.3. Ms: m
/
z = 311 (M+. + 1).7f: IR (KBr): 3100–3400 cm
-
1 (broad medium, –NH–), 1680 cm
-
1 (sharp, strong, –CO– of acid group), 1644 cm
-
1 (sharp, strong, –CO– of amide group); 1H-NMR: δ 1.0 (t, 6H, –CH3, –CH3), δ 2.4 (s, 3H, –CH3), δ 3.2 (q, 2H, –CH2), δ 3.4 (q, 2H, –CH2), 7.0–8.0 (m, 8H, Ar-H), 10.6 (s, 1H, –NH, D2O exchangeable). 13C NMR (DMSO-d6, 400 MHz): 12.6, 13.8, 19.4, 39.9, 43.6, 123.6, 124.6, 125.2, 126.6, 127.6, 129.8, 131.2, 133.5, 136.5, 166.7, 168.3. Ms: m
/
z = 311 (M+. + 1).7g: IR (KBr): 3100–3400 cm
-
1 (broad medium, –NH–), 1685 cm
-
1 (sharp, strong, –CO– of acid group), 1655 cm
-
1 (sharp, strong, –CO– of amide group); 1H-NMR: δ 2.2 (s, 1H, –NH), δ 2.4 (s, 3H, –CH3), δ 3.0 (t, 2H, –CH2), δ 3.2 (t, 2H, –CH2), δ 3.4 (t, 2H, –CH2), δ 3.8 (t, 2H, –CH2), 7.0–8.0 (m, 8H, Ar-H), 10.6 (s, 1H, –NH, D2O exchangeable). 13C NMR (DMSO-d6, 400 MHz): 20.5, 44.5, 49.3, 50.5, 51.5, 120.2, 122.4, 123.4, 124.5, 125.3, 126.6, 128.5, 130.1, 133.5, 163.7, 166.6. Ms: m
/
z = 324 (M+. + 1).7h: IR (KBr): 3100–3400 cm
-
1 (broad medium, –NH–), 1695 cm
-
1 (sharp, strong, –CO– of acid group), 1655 cm
-
1 (sharp, strong, –CO– of amide group); 1H-NMR: δ 1.2 (t, 3H, –CH3), δ 2.4 (s, 3H, –CH3), δ 2.6 (q, 2H, –CH2), δ 3.0 (t, 2H, –CH2), δ 3.2 (t, 2H, –CH2), δ 3.4 (t, 2H, –CH2), δ 3.8 (t, 2H, –CH2), 7.0–8.0 (m, 8H, Ar-H), 10.6 (s, 1H, –NH, D2O exchangeable). 13C NMR (DMSO-d6, 400 MHz): 12.2, 19.3, 44.2, 47.6, 48.3, 51.2, 52.2, 119.3, 121.3, 124.2, 124.9, 126.2, 127.1, 130.4, 131.3, 132.3, 161.1, 165.1. Ms: m
/
z = 352 (M+. + 1).7i: IR (KBr): 3100–3400 cm
-
1 (broad medium, –NH–), 1680 cm
-
1 (sharp, strong, –CO– of acid group), 1650 cm
-
1 (sharp, strong, –CO– of amide group); 1H-NMR: δ 1.6 (t, 3H, –CH3), δ 2.4 (s, 3H, –CH3), δ 3.0 (t, 2H, –CH2), δ 3.2 (t, 2H, –CH2), δ 3.4 (t, 2H, –CH2), δ 3.8 (t, 2H, –CH2), 7.0–8.0 (m, 8H, Ar-H), 13.00 (s, 1H, –NH, D2O exchangeable). 13C NMR (DMSO-d6, 400 MHz): 18.4, 35.4, 45.4, 46.3, 47.3, 51.3, 120.1, 122.2, 122.6, 124.5, 124.7, 127.4, 128.6, 131.0, 132.8, 164.6, 169.9. Ms: m
/
z = 338 (M+. + 1).7j: IR (KBr): 3100–3400 cm
-
1 (broad medium, –NH–), 1685 cm
-
1 (sharp, strong, –CO– of acid group), 1650 cm
-
1 (sharp, strong, –CO– of amide group); 1H-NMR: δ 2.4 (s, 3H, –CH3), δ 3.0 (t, 2H, –CH2), δ 3.2 (t, 2H, –CH2), δ 3.4 (t, 2H, –CH2), δ 3.8 (t, 2H, –CH2), 7.0–8.0 (m, 8H, Ar-H), 13.00 (s, 1H, –NH, D2O exchangeable). 13C NMR (DMSO-d6, 400 MHz): 17.9, 51.2, 52.0, 70.2, 72.4, 121.2, 122.4, 125.3, 126.0, 126.9, 127.0, 129.6, 130.1, 131.5, 160.4, 166.7. Ms: m
/
z = 325 (M+. + 1).7k: IR (KBr): 3100–3400 cm
-
1 (broad medium, –NH–), 1685 cm
-
1 (sharp, strong, –CO– of acid group), 1645 cm
-
1 (sharp, strong, –CO– of amide group); 1H-NMR: δ 1.1 (t, 6H, –CH3, –CH3), δ 2.6 (s, 3H, –CH3), δ 3.2 (q, 2H, –CH2), δ 3.4 (q, 2H, –CH2), 7.0–8.0 (m, 8H, Ar-H), 10.6 (s, 1H, –NH, D2O exchangeable). 13C NMR (DMSO-d6, 400 MHz): 12.4, 13.5, 19.6, 40.9, 43.5, 124.6, 125.6, 126.7, 128.6, 129.4, 130.6, 131.2, 136.5, 135.5, 166.9, 168.7. Ms: m
/
z = 311 (M+. + 1).7l: IR (KBr): 3100–3400 cm
-
1 (broad medium, –NH–), 1685 cm
-
1 (sharp, strong, –CO– of acid group), 1655 cm
-
1 (sharp, strong, –CO– of amide group); 1H-NMR: δ 2.4 (s, 1H, –NH), δ 2.4 (s, 3H, –CH3), δ 3.0 (t, 2H, –CH2), δ 3.4 (t, 2H, –CH2), δ 3.4 (t, 2H, –CH2), δ 3.8 (t, 2H, –CH2), 7.0–8.0 (m, 8H, Ar-H), 10.6 (s, 1H, –NH, D2O exchangeable). 13C NMR (DMSO-d6, 400 MHz): 19.5, 43.4, 45.5, 52.5, 53.4, 119.3, 123.4, 123.9, 124.9, 125.5, 127.6, 128.7, 130.2, 132.5, 161.3, 166.5. Ms: m
/
z = 324 (M+. + 1).7m: IR (KBr): 3100–3400 cm
-
1 (broad medium, –NH–), 1695 cm
-
1 (sharp, strong, –CO– of acid group), 1655 cm
-
1 (sharp, strong, –CO– of amide group); 1H-NMR: δ 1.4 (t, 3H, –CH3), δ 2.4 (s, 3H, –CH3), δ 2.6 (q, 2H, –CH2), δ 3.0 (t, 2H, –CH2), δ 3.2 (t, 2H, –CH2), δ 3.4 (t, 2H, –CH2), δ 3.8 (t, 2H, –CH2), 7.0–8.0 (m, 8H, Ar-H), 10.4 (s, 1H, –NH, D2O exchangeable). 13C NMR (DMSO-d6, 400 MHz): 11.23, 18.2, 42.1, 43.4, 45.2, 50.8, 51.3, 119.5, 120.4, 124.5, 126.9, 127.4, 126.1, 130.6, 131.3, 132.6, 160.1, 165.6. Ms: m
/
z = 352 (M+. + 1).7n: IR (KBr): 3100–3400 cm
-
1 (broad medium, –NH–), 1683 cm
-
1 (sharp, strong, –CO– of acid group), 1650 cm
-
1 (sharp, strong, –CO– of amide group); 1H-NMR: δ 1.6 (t, 3H, –CH3), δ 2.4 (s, 3H, –CH3), δ 3.0 (t, 2H, –CH2), δ 3.2 (t, 2H, –CH2), δ 3.4 (t, 2H, –CH2), δ 3.8 (t, 2H, –CH2), 7.0–8.0 (m, 8H, Ar-H), 13.00 (s, 1H, –NH, D2O exchangeable). 13C NMR (DMSO-d6, 400 MHz): 18.3, 36.3, 43.5, 45.2, 46.2, 50.2, 121.2, 121.1, 122.4, 124.4, 125.6, 126.3, 127.2, 130.0, 131.4, 162.6, 166.8. Ms: m
/
z = 338 (M+. + 1).7o: IR (KBr): 3100–3400 cm
-
1 (broad medium, –NH–), 1685 cm
-
1 (sharp, strong, –CO– of acid group), 1650 cm
-
1 (sharp, strong, –CO– of amide group); 1H-NMR: δ 2.4 (s, 3H, –CH3), δ 3.0 (t, 2H, –CH2), δ 3.2 (t, 2H, –CH2), δ 3.4 (t, 2H, –CH2), δ 3.8 (t, 2H, –CH2), 7.0–8.0 (m, 8H, Ar-H), 13.00 (s, 1H, –NH, D2O exchangeable). 13C NMR (DMSO-d6, 400 MHz): 18.5, 50.1, 51.6, 73.5, 74.3, 119.2, 120.2, 121.2, 122.1, 123.4, 124.1, 125.3, 127.3, 128.3, 163.5, 167.4. Ms: m
/
z = 325 (M+. + 1).7p: IR (KBr): 3100–3400 cm
-
1 (broad medium, –NH–), 1670 cm
-
1 (sharp, strong, –CO– of acid group), 1655 cm
-
1 (sharp, strong, –CO– of amide group); 1H-NMR: δ 1.0 (t, 6H, –CH3, –CH3), δ 2.4 (s, 3H, –CH3), δ 3.2 (q, 2H, –CH2), δ 3.4 (q, 2H, –CH2), 7.0–8.0 (m, 8H, Ar-H), 10.6 (s, 1H, –NH, D2O exchangeable). 13C NMR (DMSO-d6, 400 MHz): 12.4, 14.4, 32.9, 40.5, 121.4, 125.8, 126.8, 129.1, 130.3, 131.4, 134.6, 138.4, 139.9, 163.6, 169.9. Ms: m
/
z = 331 (M+. + 1).7q: IR (KBr): 3100–3400 cm
-
1 (broad medium, –NH–), 1684 cm
-
1 (sharp, strong, –CO– of acid group), 1650 cm
-
1 (sharp, strong, –CO– of amide group); 1H-NMR: δ 2.2 (s, 1H, –NH), δ 2.4 (s, 3H, –CH3), δ 3.0 (t, 2H, –CH2), δ 3.2 (t, 2H, –CH2), δ 3.4 (t, 2H, –CH2), δ 3.8 (t, 2H, –CH2), 7.0–8.0 (m, 8H, Ar-H), 10.4 (s, 1H, –NH, D2O exchangeable). 13C NMR (DMSO-d6, 400 MHz): 44.5, 44.9, 53.2, 54.2, 119.6, 120.5, 121.9, 122.9, 127.5, 128.5, 129.6, 130.2, 131.3, 162.4, 164.2. Ms: m
/
z = 344 (M+. + 1).7r: IR (KBr): 3100–3400 cm
-
1 (broad medium, –NH–), 1650 cm
-
1 (sharp, strong, –CO– of acid group), 1640 cm
-
1 (sharp, strong, –CO– of amide group); 1H-NMR: δ 1.2 (t, 3H, –CH3), δ 2.4 (s, 3H, –CH3), δ 2.6 (q, 2H, –CH2), δ 3.0 (t, 2H, –CH2), δ 3.2 (t, 2H, –CH2), δ 3.4 (t, 2H, –CH2), δ 3.8 (t, 2H, –CH2), 7.0–8.0 (m, 8H, Ar-H), 10.4 (s, 1H, –NH, D2O exchangeable). 13C NMR (DMSO-d6, 400 MHz): 12.8, 44.2, 45.4, 46.2, 51.8, 52.4, 119.6, 121.5, 124.5, 125.6, 127.3, 125.6, 130.2, 132.4, 135.7, 160.7, 165.9. Ms: m
/
z = 372 (M+. + 1).7s: IR (KBr): 3100–3400 cm
-
1 (broad medium, –NH–), 1640 cm
-
1 (sharp, strong, –CO– of acid group), 1635 cm
-
1 (sharp, strong, –CO– of amide group); 1H-NMR: δ 1.6 (t, 3H, –CH3), δ 2.4 (s, 3H, –CH3), δ 3.0 (t, 2H, –CH2), δ 3.2 (t, 2H, –CH2), δ 3.4 (t, 2H, –CH2), δ 3.8 (t, 2H, –CH2), 7.0–8.0 (m, 8H, Ar-H), 13.00 (s, 1H, –NH, D2O exchangeable). 13C NMR (DMSO-d6, 400 MHz): 38.3, 45.6, 46.2, 47.5, 50.6, 123.2, 126.6, 127.3, 128.3, 129.1, 129.9, 130.2, 131.4, 132.4, 160.3, 166.4. Ms: m
/
z = 358 (M+. + 1).7t: IR (KBr): 3100–3400 cm
-
1 (broad medium, –NH–), 1690 cm
-
1 (sharp, strong, –CO– of acid group), 1650 cm
-
1 (sharp, strong, –CO– of amide group); 1H-NMR: δ 2.4 (s, 3H, –CH3), δ 3.0 (t, 2H, –CH2), δ 3.2 (t, 2H, –CH2), δ 3.4 (t, 2H, –CH2), δ 3.8 (t, 2H, –CH2), 7.0–8.0 (m, 8H, Ar-H), 13.00 (s, 1H, –NH, D2O exchangeable). 13C NMR (DMSO-d6, 400 MHz): 48.1, 50.6, 72.5, 73.1, 119.5, 120.6, 122.3, 122.9, 123.5, 124.3, 125.7, 126.3, 129.3, 165.7, 169.4. Ms: m
/
z = 345 (M+. + 1).7u: IR (KBr): 3100–3400 cm
-
1 (broad medium, –NH–), 1680 cm
-
1 (sharp, strong, –CO– of acid group), 1650 cm
-
1 (sharp, strong, –CO– of amide group); 1H-NMR: δ 1.0 (t, 6H, –CH3, –CH3), δ 2.4 (s, 3H, –CH3), δ 3.2 (q, 2H, –CH2), δ 3.4 (q, 2H, –CH2), 7.0–8.0 (m, 9H, Ar-H), 10.6 (s, 1H, –NH, D2O exchangeable). 13C NMR (DMSO-d6, 400 MHz): 12.5, 15.4, 37.9, 43.5, 125.4, 126.5, 126.8, 129.6, 131.2, 131.3, 135.6, 138.6, 139.3, 164.6, 169.8. Ms: m
/
z = 375 (M+. + 1).7v: IR (KBr): 3100–3400 cm
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1 (broad medium, –NH–), 1687 cm
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1 (sharp, strong, –CO– of acid group), 1655 cm
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1 (sharp, strong, –CO– of amide group); 1H-NMR: δ 2.2 (s, 1H, –NH), δ 2.4 (s, 3H, –CH3), δ 3.0 (t, 2H, –CH2), δ 3.2 (t, 2H, –CH2), δ 3.4 (t, 2H, –CH2), δ 3.8 (t, 2H, –CH2), 7.0–8.0 (m, 9H, Ar-H), 13.00 (s, 1H, –NH, D2O exchangeable). 13C NMR (DMSO-d6, 400 MHz): 41.5, 45.9, 52.3, 54.5, 118.4, 121.3, 125.9, 126.9, 127.7, 128.4, 129.7, 131.4, 133.5, 165.4, 167.7. Ms: m
/
z = 388 (M+. + 1).7w: IR (KBr): 3100–3400 cm
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1 (broad medium, –NH–), 1681 cm
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1 (sharp, strong, –CO– of acid group), 1655 cm
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1 (sharp, strong, –CO– of amide group); 1H-NMR: δ 1.2 (t, 3H, –CH3), δ 2.4 (s, 3H, –CH3), δ 2.6 (q, 2H, –CH2), δ 3.0 (t, 2H, –CH2), δ 3.2 (t, 2H, –CH2), δ 3.4 (t, 2H, –CH2), δ 3.8 (t, 2H, –CH2), 7.0–8.0 (m, 9H, Ar-H), 10.4 (s, 1H, –NH, D2O exchangeable). 13C NMR (DMSO-d6, 400 MHz): 12.4, 43.5, 45.7, 47.3, 52.9, 53.4, 118.4, 121.6, 124.7, 125.5, 128.3, 129.5, 130.5, 131.3, 135.4, 164.5, 165.9. Ms: m
/
z = 416 (M+. + 1).7x:IR (KBr): 3100–3400 cm
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1 (broad medium, –NH–), 1690 cm
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1 (sharp, strong, –CO– of acid group), 1658 cm
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1 (sharp, strong, –CO– of amide group); 1H-NMR: δ 1.6 (t, 3H, –CH3), δ 2.4 (s, 3H, –CH3), δ 3.0 (t, 2H, –CH2), δ 3.2 (t, 2H, –CH2), δ 3.4 (t, 2H, –CH2), δ 3.8 (t, 2H, –CH2), 7.0–8.0 (m, 9H, Ar-H), 13.00 (s, 1H, –NH, D2O exchangeable). 13C NMR (DMSO-d6, 400 MHz): 39.2, 46.4, 47.3, 48.4, 49.5, 121.2, 124.3, 124.9, 125.7, 126.4, 128.3, 130.6, 131.1, 131.3, 166.1, 169.3. Ms: m
/
z = 402 (M+. + 1).7y: IR (KBr): 3100–3400 cm
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1 (broad medium, –NH–), 1675 cm
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1 (sharp, strong, –CO– of acid group), 1635 cm
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1 (sharp, strong, –CO– of amide group); 1H-NMR: δ 2.4 (s, 3H, –CH3), δ 3.0 (t, 2H, –CH2), δ 3.2 (t, 2H, –CH2), δ 3.4 (t, 2H, –CH2), δ 3.8 (t, 2H, –CH2), 7.0–8.0 (m, 9H, Ar-H), 13.00 (s, 1H, –NH, D2O exchangeable). 13C NMR (DMSO-d6, 400 MHz): 48.9, 51.4, 73.5, 74.5, 119.6, 121.4, 122.5, 123.8, 124.7, 125.7, 126.4, 127.3, 129.3, 165.8, 169.3. Ms: m
/
z = 389 (M+. + 1).



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*Source: 576715-2014-05-05.xml*