In this work, a rapid and high yield synthetic method for N-(4-fluorophenyl)-1-(pyrrolidine-1-carbonyl) cyclopropane-1-carboxamide (8) was established. The target compound 8 was synthesized from the commercially available 1-(methoxycarbonyl) cyclopropane-1-carboxylic acid (5) via multi-step nucleophilic substitution reaction and ester hydrolysis. The structure of the target compound was confirmed by 1H NMR and MS spectrum. The total yield of the three steps was 48.8%.

1.
Obstetrics and Gynecology Branch of Chinese Medical Association Obstetrics and Gynecology Branch
.
Guidelines for prevention and treatment of postpartum hemorrhage
.
Chinese Journal of Obstetrics and Gynecology
,
2014
,
49
(
9
):
641
646
.
2.
Mcguire
S.
World Cancer Report 2014. Geneva, Switzerland: World Health Organization, International Agency for Research on Cancer, WHO Press, 2015
.
Advances in Nutrition
,
2016
,
7
(
2
):
418
419
.
3.
Aliebrahimi
S.
,
Montasser
S. K.
,
Ostad
S. N.
, et al. 
Identification of Phytochemicals Targeting c-Met Kinase Domain using Consensus Docking and Molecular Dynamics Simulation Studies
.
Cell Biochemistry & Biophysics
,
2017
:
1
11
.
4.
Zhai
X.
,
Bao
G.
,
Wang
L.
, et al. 
Design, synthesis and biological evaluation of novel 4-phenoxy-6, 7-disubstituted quinolines possessing (thio) semicarbazones as c-Met kinase inhibitors
.
Bioorganic & medicinal chemistry
,
2016
,
24
(
6
):
1331
1345
.
5.
Maroun
C.R.
,
Rowlands
T.
The Met receptor tyrosine kinase: a key player in oncogenesis and drug resistance
.
Pharmacol Ther
,
2014
,
142
(
3
):
316
338
.
6.
Baljevic
M.
,
Zaman
S.
,
Baladandayuthapani
V.
, et al. 
Phase II study of the c-MET inhibitor tivantinib (ARQ 197) in patients with relapsed or relapsed/refractory multiple myeloma
.
Annals of hematology
,
2017
,
96
(
6
):
977
985
.
7.
Lv
P. C.
,
Wang
Z. C.
,
Zhu
H. L.
Recent advances in the design and synthesis of c-Met inhibitors as anticancer agents (2014-present
).
Current medicinal chemistry
,
2017
,
24
(
1
):
57
64
.
8.
Kim
H. J.
,
Jung
M. H.
,
Kim
H.
, et al. 
Synthesis and antiproliferative activity of pyrrolo[3,2-b]pyridine derivatives against melanoma
.
Bioorganic & Medicinal Chemistry Letters
,
2010
,
20
(
1
):
413
417
.
9.
You
W.
,
Sennino
B.
,
Williamson
C. W.
, et al. 
VEGF and c-Met blockade amplify angiogenesis inhibition in pancreatic islet cancer
.
Cancer Research
,
2011
,
71
(
14
):
4758
4768
.
10.
Y.
Kataoka
,
T.
Mukohara
,
H.
Tomioka
, et al.,
Foretinib (GSK1363089), a multikinase inhibitor of MET and VEGFRs, inhibits growth of gastric cancer cell lines by blocking inter-receptor tyrosine kinase networks
.
Investigational New Drugs
,
2012
,
30
(
4
):
1352
1360
.
11.
Zhao
Y.
,
Zhang
J.
,
Zhuang
R.
, et al. 
Synthesis and evaluation of a series of pyridine and pyrimidine derivatives as type II c-Met inhibitors
.
Bioorganic & Medicinal Chemistry
,
2017
,
25
(
12
):
3195
3205
.
12.
Qiang
H.
,
Gu
W.
,
Huang
D.
, et al. 
Design, synthesis and biological evaluation of 4-aminopyrimidine-5-cabaldehyde oximes as dual inhibitors of c-Met and VEGFR-2
.
Bioorganic & Medicinal Chemistry
,
2016
,
24
(
16
):
3353
3358
.
This content is only available via PDF.
You do not currently have access to this content.