Synthesis of maleopimaric and citraconopimaric acids N-[3-(pyrimidin-2-yl) aryl]amides

Article abstract of DOI:10.1134/S1070428012080143

Acylation of 6-methyl-N-[4-(pyridin-3-yl)pyrimidin-2-yl]benzene-1,3- diamine, 4-methyl-N-[4-(pyridin- 3-yl)pyrimidin-2-yl]benzene-1,3-diamine, and N-[4-(pyridin-3-yl)pyrimidin-2-yl]benzene-1,3-diamine with maleopimaric and citraconopimaric acid chlorides,

Full text of DOI:10.1134/S1070428012080143

ISSN 1070-4280, Russian Journal of Organic Chemistry, 2012, Vol. 48, No. 8, pp. 1121−1125. © Pleiades Publishing, Ltd., 2012.
Original English Text © E.V. Koroleva, K.N. Gusak, Zh.V. Ignatovich, A.L. Ermolinskaya, M.P. Bei, A.P. Yuvchenko, 2012, published in Zhurnal Organicheskoi
Khimii, 2012, Vol. 48, No. 8, pp. 1122−1126.
Synthesis of Maleopimaric and Citraconopimaric Acids
N-[3-(Pyrimidin-2-yl)aryl]amides
E. V. Koroleva, K. N. Gusak, Zh. V. Ignatovich, A. L. Ermolinskaya,
M. P. Bei, and A. P. Yuvchenko
Institute of New Materials Chemistry of National Academy of Belarus, Academy of Sciences of Belarus,
Minsk, 220141 Belarus’
e-mail: evk@ichnm.basnet.by
Received November 7, 2011
Abstract—Acylation of 6-methyl-N-[4-(pyridin-3-yl)pyrimidin-2-yl]benzene-1,3-diamine, 4-methyl-N-[4-(pyridin-
3-yl)pyrimidin-2-yl]benzene-1,3-diamine, and N-[4-(pyridin-3-yl)pyrimidin-2-yl]benzene-1,3-diamine with
maleopimaric and citraconopimaric acid chlorides, with benzotriazolyl maleopimarate afforded N-[3-(pyrimidin-
2-yl)aryl]amides of maleopimaric and citraconopimaric acids. By the reaction of substituted N-arylamides of
maleopimaric acid with methanesulfonic acid biologically active methanesulfonates were obtained.
DOI: 10.1134/S1070428012080143
Due to the high physiological activity the
2-aminopyrimidine derivatives are promising for the
application as bioactive substances with a wide range of
therapeutical action. They are the active substances of
known drugs like fluorofur, acyclovir, trimethoprim, rosu-
vastatin [1]. Based on 2-arylaminopyrimidine derivatives
antitumor drugs glivec (imatinib) and tasigna (nilotinib)
has been developed that are now the most efficient drugs
in the treatment of chronic myeloid leukemia [2, 3]. The
high price of glivec and tasigna and the resistance to the
medical treatment in some cases call to the search for and
development of analogs of these drugs.
itself exhibited pronounced hepatoprotective, immunos-
timulating action, fungicidal and other properties [5, 7–9].
Maleopimaric (I) and citraconopimaric (II) acids are
obtained from wood chemical raw material, purified and
described in [10–12]. The derivatives of citraconopimaric
acid except for its methyl, allyl, and propargyl esters were
not obtained before.
We for the first time brought into the synthesis of
amides from the derivatives of maleopimaric (I) and
citraconopimaric (II) acids 6-methyl-N-[4-(pyridin-3-
yl)pyrimidin-2-yl]benzene-1,3-diamine (III), the key
precursor of the imatinib substance, its isomer 4-methyl-
N-[4-(pyridin-3-yl)pyrimidin-2-yl]benzene-1,3-diamine
(IV), and the demethylated analog N-[4-(pyridin-3-yl)
pyrimidin-2-yl]benzene-1,3-diamine (V).
In the structure of the active substance of imatinib
one of the main pharmacophoric fragments is the
amide group binding N-(2-methyl-5-aminophenyl)-
4-(pyridin-3-yl)pyrimidin-2-amine and the residue of
the 4-(4-methylpiperazin-1-yl)methylbenzoic acid.
We describe here the synthesis of new analogs of the
active substance of imatinib containing instead of the
benzylpiperazine fragment a residue of maleopimaric or
citraconopimaric acid.
The amides were synthesized by acylation of amines
III–V with acid chlorides VI, VII of maleopimaric and
citraconopimaric acids (procedure а) and with activated
ester VIII of acid I and hydroxybenzotriazole (procedure
b) [13, 14]. Acid chlorides VI, VII were obtained by
treating acids I, II with excess thionyl chloride.
Methods were developed for the preparation of a
number of maleopimaric acid derivatives at the carboxy
and anhydride groups, in particular, of N-aryl- and N-
alkylamides, imides, amidoimides [4–6]. Amides and
imidoamides of the maleopimaric acid and also the acid
By procedure a compounds III–V were acylated with
an excess of the corresponding acid chloride VI, VII in
THF in the presence of triethylamine (Et3N). Amides
IX–XII of maleopimaric and citraconopimaric acids were
obtained in 40–78% yields.
1121

KOROLEVA et al.
1122
Scheme.
Me
HO
Me
Me
O
Me
SOCl2,
MeC6H5
DCC, HOBt,
CH2Cl2, DMAP
R1
25oC
20oC
O
O
O
I, II
N
N
Me
N
Cl
Me
Me
O
Me
O
O
Me
Me
Me
O
O
Me
R1
O
R1
O
VI, VII
O
O
N
VIII
N
N
R2
HN
III, V
a
b
R3
N
III_V
NH2
N
R2
R3
Me
O
H
N
N
H
Me
Me
N
Me
R1
O
O
O
IX_XII
R2
N
R3
Me
O
H
N
N
H
N
CH3SO3H
Me
IX, XI
Me
N
.
CH3SO3H
Me
R1
O
O
O
XIII, XIV
(а) Et3N, THF, 45°С; (b) DMAP, CH2Cl2, 25°C; R1 = H (I, VI, VIII), Me (II, VII); R2 = Me, R3 = H (III); R2 = H, R3 =
Me (IV), R2 = R3 = H (V); R1 = R3 = H, R2 = Me (IX, XIII); R1 = R2 = H, R3 = Me (X); R1 = R2 = R3 = H (XI, XIV); R1 =
R2 = Mе, R3 = H (XII).
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 48 No. 8 2012

SYNTHESIS OF MALEOPIMARIC AND CITRACONOPIMARIC ACIDS
1123
The acylation of amines III–V by method b
was carried out in two steps. First from acid I,
1-hydroxybenzotriazole (HOBt), and dicyclo-
hexylcarbodiimide (DCC) ester VIII was prepared, in
the second stage the amine was added, and the reaction
was performed in the presence of catalytic quantities of
2-dimethylaminopyridine (DMAP). The application of
procedure b makes it possible to avoid heating of the
reaction mixture, but it takes longer time than acylation
with the acid chlorides.
In the IR spectra of methansulfonates XIII, XIV
alongside the characteristic bands of initial amides a band
of the stretching vibrations of the S=O group is pres-
ent at 1150–1140 cm–1. In the 1Н NMR spectra of salts
compared to the spectra of amides a singlet appears of
the protons of the methyl group of the methanesulfonate
moiety at 2.60–2.65 ppm.
EXPERIMENTAL
IR spectra were recorded on a Fourier spectrometer
Nicolet Protege-460 from pellets with KBr. Н NMR
The maximum yield (78%) was obtained from amine
V lacking the methyl group in the aniline fragment of the
molecule. The sufficiently high yield of amides IX, XII
(48–58%) was obtained from amine III. The lower yield
of amide X (40%) is evidently due to the steric hindrance
from the о-methyl group in the molecule of amine IV.
1
spectra were registered on a spectrometer BrukerAvance
АС-500 (500 and 100 MHz) in CDCl3 (for amides) and
methanol (d4) (for salts); internal reference TMS. TLC
was carried out on Merk DC-Plasticfolien Kieselgel 60
F254 plates, eluents butanol−ethanol–NH4OH, 8 : 1 : 1,
and chloroform–methanol, 95 : 5. Melting points were
determined on a Koeffler heating block.
At low temperature (20–65°С) the anhydride group
of the maleopimaric and citraconopimaric acids is not
involved into processes of chloroacylation, esterification,
and aminolysis, and the reactions proceed selectively at
the carboxy group.
Amines III–V were prepared by procedure [16].
Maleopimaric and citraconopimaric acid chlorides
(VI, VII). To 3 mmol of acid I, II (for acid I in toluene)
was added 3 ml (40 mmol) of thionyl chloride, the reac-
tion mixture was stirred for 8–10 h, later it was thoroughly
evaporated in a vacuum.
Amides IX–XII were identified by spectral methods.
The IR spectra of compounds IX–XII contain charac-
teristic bands of the stretching vibrations of the C=O
bonds of the amide (1680–1660) and anhydride (1840–
1770 cm–1) fragments, of the stretching (3440–3350)
and bending (1640–1610 cm–1) vibrations of the amino
groups.
In the 13C NMR spectra of amides IX–XII the proton
signals of the N-aryl substituents (of pyridine, pyrimidine,
benzene rings and amino groups), except for the proton
signals of the methyl group (singlet at 2.27–2.33 ppm) are
located in the region of the signals of aromatic protons
(6.90–9.32 ppm). The characteristic proton signals of
the methyl groups of the acid residue appear at 0.57–0.65,
0.96–1.00, 1.18–1.36 ppm, and of the vinyl proton at the
bridging double bond, in the region 5.46–5.57 ppm.
Maleopimaroyl chloride (VI). Yield 99%, colorless
crystals, mp 190°С (decomp.) (cf. [17]). IR spectrum,
ν, cm–1: 1850, 1790 [(С=О)2О], 1710 [(C=O)Cl], 1250
[CH(CH3)2]. Found, %: С 68.82; Н 7.45; Cl 8.47.
C24H31ClO4. Calculated, %: С 68.80; Н 7.46; Cl 8.46.
Citraconopimaroyl chloride (VII). Yield 99%,
colorless crystals, mp 154–156°С. IR spectrum, ν,
cm–1: 1850, 1780 [(С=О)2О], 1700 [(C=O)Cl], 1250
[CH(CH3)2]. 1Н NMR spectrum, δ, ppm: 0.63 s (3H,
Mе), 0.97 m (1Н, СН), 1.00 d (6H, Mе2СН, J 7.0 Hz),
1.28 s (3Н, Mе), 1.36 m (2Н, СН2), 1.45 s (3H, Mе),
1.47−1.78 m (10Н, СН2), 2.25 sextet (1H, Mе2CH),
2.34 m (1Н, СН), 2.61 d (1Н, СН, J 3.0 Hz), 3.05 s (1Н,
СН), 5.59 s (1Н, СН=С). Found, %: С 69.34; Н 7.65;
Cl 8.17. C25H33ClO4. Calculated, %: С 69.35; Н 7.68;
Cl 8.19.
In the 13СNMR spectrum of citraconopimaric acid
amide XII the signals of the aliphatic carbon atoms appear
in the region 8.30–65.54 ppm, of aromatic carbon atoms,
at 108.00–158.78 ppm. The signals of carbon atoms of
the carbonyl groups are at 162.40, 172.41, 176.31 ppm.
Acylation of 2-arylaminopyrimidines III–V. а.
To a solution of 0.01 mol of 2-arylaminopyrimidine
III–V in 10 ml of THF was added 0.02 mol of triethyl-
amine, the mixture was heated at 60–65°С for 30 min,
then 0.013 mol of maleopimaroyl chloride (VI) or
citraconopimaroyl chloride (VII) was added, the mixture
was stirred at 60–65°С over 4–6 h. On the completion
In order to prepare pharmacologicaly active sub-
stances for the estimation of the physiologic action we
obtained salts XIII, XIV of compounds IX, XI with
methanesulfonic acid by the procedure of the synthesis
of imatinib methanesulfonate [15].
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 48 No. 8 2012

KOROLEVA et al.
1124
Maleopimaric acid N-{3-[4-(Pyridin-3-yl)
pyrimidin-2-yl-amino]phenyl}amide (XI). Yield 78%
(а), 69% (b), colorless crystals, mp 186–187°С. IR
spectrum, cm–1: 3440–3350, 2880, 1840, 1785, 1670,
of the reaction (TLC monitoring) with the solvent was
evaporated in a vacuum, the residue was treated with 20%
water solution of NaOH to рН 9. The reaction product
was extracted into chloroform (3 × 40 ml), the extract
was dried over MgSO4, chloroform was removed in a
vacuum. The obtained amide was recrystallized from a
mixture ethyl acetate–ethyl ether.
1
1640, 1570, 1320, 1270. Н NMR spectrum, δ, ppm:
0.57 s (3Н, Mе), 0.78 t (1Н, СН, J 11.8 Hz), 0.96 d (3Н,
Mе, J 1.9 Hz), 0.97 d (3Н, Mе, J 1.9 Hz), 1.15–1.27 m
(4Н, СН2), 1.33 s (3Н, Mе), 1.39–1.55 m (6Н, СН2),
1.90 d (1Н, СН, J 11.8 Hz), 2.20 m (3Н, CH, СН2), 2.32 m
(1Н, СН), 2.99 d.d (1Н, СН, J 8.8, 3.1 Hz), 3.05 s (1Н,
СН), 5.46 s (1Н, СН=С), 6.90 d (1Нarom, J 8.8 Hz), 7.19 d
(1Нarom, J 5.2 Hz), 7.31 t (1Нarom, J 8.0 Hz), 7.43 d.d
b. A solution of 0.4 g (1 mmol) of maleopimaric acid
(I) and 0.34 g (1.5 mmol) of DСС in 20 ml of dichloro-
methane was stirred at room temperature for 10 min, and
0.24 g (1.8 mmol) of 1-hydroxybenzotriazole was added.
The reaction mixture was stirred at room temperature
over 15–18 h, then the precipitate of dicyclohexylurea
was filtered off and washed with dichloromethane (3 ×
20 ml). To the combined filtrates was added 1 mmol of
compound III or V, 0.05 g (catalytic amount) of DMAP,
and the reaction mixture was stirred at 18–20°С over 36 h.
On the completion of the reaction (TLC monitoring) the
mixture was diluted with 10 ml of water, 5 ml of 25%
NH4OH, the reaction product was extracted over dichlo-
romethane (3 × 20 ml), the extract was dried over Na2SO4
and evaporated in a vacuum. The solid residue of amide
was recrystallized from a mixture chloroform–ethyl ether.
(1Нarom, J 7.9, 4.8 Hz), 7.70 s (1Н, NH), 7.82 d (1Нarom
J 8.5 Hz), 8.29 s (1Нarom), 8.36 s (1Нarom), 8.43 d.t (1Нarom
J 8.0, 1.9 Hz), 8.54 d (1Нarom, J 5.1 Hz), 8.72 d.d (1Нarom
,
,
,
J 4.2, 1.6 Hz), 9.29 d (1Н, NH, J 1.9 Hz). Found, %:
С 72.52; Н 6.72; N 10.83. C39H43N5O4. Calculated, %:
С 72.53; Н 6.71; N 10.84.
Citraconopimaric acid N-{4-methyl-3-[4-(pyridin-
3-yl)pyrimidin-2-ylamino]phenyl}amide (XII). Yield
48% (а), colorless crystals, mp 176–178°С. IR spectrum,
cm–1: 3400–3350, 2980, 1850, 1790, 1740, 1660, 1580,
1
1430, 1310, 1250. Н NMR spectrum, δ, ppm: 0.65 s
(3Н, Me), 0.99 d (6Н, Me2, J 6.7 Hz), 1.20 m (2Н, СН2),
1.32 s (3Н, Mе), 1.36 s (3Н, Mе), 1.46–1.64 m (8Н, СН2),
1.70 m (1Н, СН), 1.83 d (1Н, СН, J 7.8 Hz), 2.04 s (1Н,
СН), 2.23 m (2Н, СН2), 2.33 s (3Н, Mе), 2.57 d (1Н, СН,
J 2.6 Hz), 3.02 s (1Н, СН), 5.57 s (1Н, СН=С), 7.10 s
(1Нarom), 7.24 m (3Нarom), 7.43 d.d (1Нarom, J 7.8, 4.8 Hz),
7.53 s (1Нarom), 8.40 s (1Н, NH), 8.49 d (1Нarom, J 7.8 Hz),
8.52 d (1Нarom, J 4.8 Hz), 8.72 d (1Нarom, J 4.8 Hz), 9.24 s
(1Н, NH). 13С NMR spectrum, δ, ppm: 8.30, 13.89,
16.14, 17.34, 18.22, 19.58, 20.71, 27.18, 29.49, 32.29,
36.65, 37.59, 37.92, 41.87, 45.75, 46.55, 47.24, 49.31,
52.92, 54.59, 57.63, 60.07, 65.54, 108.00, 113.30, 115.39,
123.40, 124.25, 127.44, 130.41, 132.43, 134.58, 136.06,
137.40, 147.29, 148.22, 151.17, 158.78, 162.40, 172.41,
176.31. Found, %: С 73.10; Н 7.04; N 10.38. C41H47N5O4.
Calculated, %: С 73.08; Н 7.03; N 10.39.
Maleopimaric acid N-{4-methyl-3-[4-(pyridin-
3-yl)pyrimidin-2-ylamino]phenyl}amide (IX). Yield
58% (а), 56% (b), colorless crystals, mp 161–162°С. IR
spectrum, cm–1: 3440, 2870, 1795, 1670, 1610, 1580,
1
1450, 1320, 1275. Н NMR spectrum, δ, ppm: 0.59 s
(3Н, Mе), 0.97 d (1Н, СН, J 9.0 Hz), 1.00 m (6Н, Mе2),
1.18 m (3Н, Mе), 1.25–1.89 m (8Н, СН2), 2.01 s (1Н,
СН), 2.05 s (1Н, СН), 2.30 s (3Н, Mе), 2.51–3.10 m (7Н,
СН, СН2), 5.54 s (1Н, СН=С), 7.15–7.20 m (3Нarom
,
NH), 7.44 m (2Нarom), 7.58 d (1Нarom, J 7.4 Hz), 7.78
m (1Нarom), 8.40–8.46 m (2Нarom), 8.72 m (1Нarom),
9.32 s (1Н, NH). Found, %: С 72.83; Н 6.86; N 10.62.
C40H45N5O4. Calculated, %: С 72.81; Н 6.87; N 10.61.
Maleopimaric acid N-{2-methyl-5-[4-(pyridin-3-yl)
pyrimidin-2-ylamino]phenyl}amide (X). Yield 40% (а),
colorless crystals, mp 177–178°С. IR spectrum, cm–1:
3440–3350, 2880, 1840, 1790, 1680, 1620, 1580, 1450,
1310, 1280. 1Н NMR spectrum, δ, ppm: 0.63 s (3Н, Mе),
0.98 d (3Н, Mе, J 3.5 Hz), 1.00 d (3Н, Mе, J 3.5 Hz),
1.32 s (3Н, Mе), 1.33–1.89 m (11Н, СН, СН2), 2.27 s (3Н,
Mе), 2.53–3.18 m (7Н, СН, СН2), 5.52 s (1Н, СН=С),
7.09–7.18 m (4Нarom), 7.42 m (2Нarom), 7.54 s (1Н,
NH), 8.45–8.51 m (2Нarom), 8.72 d (1Нarom, J 4.6 Hz),
9.25 s (1Н, NH). Found, %: С 72.80; Н 6.85; N 10.63.
C40H45N5O4. Calculated, %: С 72.81; Н 6.87; N 10.61.
Methanesulfonates XIII, XIV. To a suspension
of 0.4 mmol of amide IX, XI in 10 ml of ethanol was
added dropwise 0.04 g (0.4 mmol) of methanesulfonic
acid within 20 min. The reaction mixture was boiled
for 40 min, then it was filtered at 65°С. The filtrate was
evaporated to dryness, the residue was washed with ethyl
ether (2 × 20 ml), dissolved at heating in 30 ml of ethanol,
5 ml of water was added, and the reaction mixture was
kept at room temperature for 14–18 h. The precipitate was
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 48 No. 8 2012

SYNTHESIS OF MALEOPIMARIC AND CITRACONOPIMARIC ACIDS
1125
Chem Rev, 2010, vol.79, no. 8, pp. 655–681
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weight (~4 h).
Salt (XIII) of methanesulfonic acid and maleo-
pimaric acid N-{4-methyl-3-[4-(pyridin-3-yl)
pyrimidin-2-ylamino]phenyl}amide (IX). Yield 78%,
yellow nonhygroscopic crystals, mp 175–178°С. IR
spectrum, cm–1: 3430–3300, 2945, 1785, 1650, 1575,
1440, 1260, 1150. 1Н NMR spectrum, δ, ppm: 0.63 s (3Н,
Mе), 0.92 m (1Н, СН), 1.02 m (6Н, Mе2), 1.22 s (3Н,
Mе), 1.24–1.90 m (8Н, СН2), 2.36 s (3Н, Mе), 2.60 m
(2Н, СН2), 2.70 s (3Н, Mе), 2.74–3.27 m (7Н, СН, СН2),
5.41 s (1Н, СН=С), 7.12 d (2Нarom, J 7.8 Hz), 7.25 m
(1Нarom), 7.48 d (1Нarom), 7.83 s (1Нarom), 8.02 m (1Нarom),
8.59 m (2Нarom), 9.04 m (1Нarom). Found, %: С 64.93;
Н 6.38; N 9.19; S 4.01. C41H49N5O7S. Calculated, %:
С 65.17; Н 6.49; N 9.27; S 4.24.
Salt (XIV) of methanesulfonic acid and maleo-
pimaric acid N-{3-[4-(pyridin-3-yl)pyrimidin-2-
ylamino]-phenyl}amide (XI). Yield 98%, light-brown
nonhygroscopic crystals, mp 195–202°С. IR spectrum,
cm–1: 3450, 3350, 2950, 1790, 1650, 1580, 1450, 1240,
10. Bei, M.P., Izv. Nation. Akad. Nauk Belarusi, Ser. Khim.,
2006, no. 5, p. 13.
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2008/057291.
1
1140. Н NMR spectrum, δ, ppm: 0.61 d (3Н, Mе,
J 11.0 Hz), 0.93 t (3Н, Mе, J 2.0 Hz), 1.05 d (3Н, Mе,
J 2.0 Hz), 1.10 m (2Н, СН2), 1.24 s (3Н, Mе), 1.28–1.83 m
(10Н, СН2), 2.62 m (1Н, СН), 2.66 s (3Н, Mе), 2.76 m,
2.95 m, 2.98 m, 3.88 m (5Н, СН), 5.46 s (1Н, СН=С),
7.01 d.d (1Н, Нarom, J 8.0, 4.1 Hz), 7.26 m (2Нarom),
7.44 d (1Нarom, J 5.1 Hz), 8.08 d (1Нarom, J 1.8 Hz), 8.21 d
(1Нarom, J 8.0 Hz), 8.56 s (1Нarom), 8.89 br.s (1Нarom),
9.32 d.d (1Нarom, J 8.0, 1.8 Hz), 9.51 s (1Нarom). Found,
%: С 64.55; Н 6.21; N 9.37; S 4.17. C40H47N5O7S.
Calculated, %: С 64.78; Н 6.34; N 9.45; S 4.32.
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Kovalev, V.V., Izv. Nation. Akad. Nauk Belarusi, Ser. Khim.,
2010, no. 2, p. 84.
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