Selumetinib CAS#: 606143-52-6; 凯望编码 (ChemWhat Code): 41518

IdentificationPhysical DataSpectra
Route of Synthesis (ROS)Safety and HazardsOther Data

Identification

英文名Selumetinib
IUPAC Name6-(4-bromo-2-chloroanilino)-7-fluoro-N-(2-hydroxyethoxy)-3-methylbenzimidazole-5-carboxamide
分子结构Selumetinib-CAS-606143-52-6
CAS编号 606143-52-6
EINECS Number207-313-3
MDL NumberMFCD11977472
别名Selumetinib
606143-52-6
AZD6244
ARRY-142886
AZD 6244
5-[(4-BROMO-2-CHLOROPHENYL)AMINO]-4-FLUORO-N-(2-HYDROXYETHOXY)-1-METHYL-1H-BENZIMIDAZOLE-6-CARBOXAMIDE
AZD-6244
ARRY 142886
Selumetinib (AZD6244)
ARRY-886
selumetinibum
UNII-6UH91I579U
5-((4-bromo-2-chlorophenyl)amino)-4-fluoro-N-(2-hydroxyethoxy)-1-methyl-1H-benzo[d]imidazole-6-carboxamide
6UH91I579U
ARRY142886
Selumetinib [USAN:INN]
Koselugo
DTXSID3048944
CHEBI:90227
5-(4-broMo-2-chlorophenylaMino)-4-fluoro-N-(2-hydroxyethoxy)-1-Methyl-1H-benzo[d]iMidazole-6-carboxaMide
CHEMBL1614701
DTXCID0028870
NSC 741O78
NSC741078
NCGC00189073-01
NCGC00189073-02
1H-Benzimidazole-6-carboxamide, 5-((4-bromo-2-chlorophenyl)amino)-4-fluoro-N-(2-hydroxyethoxy)-1-methyl-
1H-Benzimidazole-6-carboxamide, 5-[(4-bromo-2-chlorophenyl)amino]-4-fluoro-N-(2-hydroxyethoxy)-1-methyl-
AZD6244 (Selumetinib)
6-(4-bromo-2-chloroanilino)-7-fluoro-N-(2-hydroxyethoxy)-3-methylbenzimidazole-5-carboxamide
5-[(4-bromo-2-chlorophenyl)amino]-4-fluoro-N-(2-hydroxyethoxy)-1-methyl-1H-1,3-benzodiazole-6-carboxamide
6-[(4-bromo-2-chlorophenyl)amino]-7-fluoro-N-(2-hydroxyethoxy)-3-methylbenzimidazole-5-carboxamide
AZD 6244;5-((4-Bromo-2-chlorophenyl)amino)-4-fluoro-N-(2-hydroxyethoxy)-1-methyl-1H-benzo[d]imidazole-6-carboxamide;6-(4-bromo-2-chlorophenylamino)-7-fluoro-N-(2-hydroxyethoxy)-3-methyl-3H-benzo[d]imidazole-5-carboxamide
CAS-606143-52-6
C17H15BrClFN4O3
3EW
5-((4-BROMO-2-CHLOROPHENYL)AMINO)-4-FLUORO-N-(2-HYDROXYETHOXY)-1-METHYL-1H-BENZIMIDAZOLE-6-CARBOXAMIDE
SELUMETINIB [MI]
SELUMETINIB [INN]
Selumetinib (USAN/INN)
SELUMETINIB [USAN]
MEK inhibitor AZD6244
SELUMETINIB [WHO-DD]
SCHEMBL155456
GTPL5665
EX-A020
CYOHGALHFOKKQC-UHFFFAOYSA-N
BCPP000367
HMS3244G03
HMS3244G04
HMS3265K01
HMS3265K02
BCP01739
Tox21_113362
BDBM50355497
MFCD11977472
NSC800882
s1008
AKOS015904255
Tox21_113362_1
BCP9000354
CCG-264774
CS-0059
DB11689
EX-8621
NSC-741078
NSC-800882
SB14707
NCGC00189073-07
6-(4-bromo-2-chloro-anilino)-7-fluoro-N-(2-hydroxyethoxy)-3-methyl-benzimidazole-5-carboxamide
AC-25059
AM808016
AZD6244,Selumetinib, ARRY-142886
HY-50706
Selumetinib (ARRY142886/AZD6244)
AZD6244 (Selumetinib,ARRY-142886)
A8446
NS00071922
SW202561-3
D09666
EN300-18166787
Q-101405
Q7448840
BRD-K57080016-001-01-9
1H-BENZIMIDAZOLE-6-CARBOXAMIDE, 5-((4-BROMO-2-CHLOROPHENYL)AMINO)-4-FLUORO-N-(2- HYDROXYETHOXY)-1-METHYL-
6-(4-bromo-2-chloro-phenylamino)-7-fluoro-3-methyl-3H-benzoimidazole-5-carboxylic acid (2-hydroxy -ethoxy)-amide
6-(4-Bromo-2-chloro-phenylamino)-7-fluoro-3-methyl-3H-benzoimidazole-5-carboxylic acid (2-hydroxy-ethoxy)-amide
6-(4-bromo-2-chloro-phenylamino)-7-fluoro-3-methyl-3H-benzoimidazole-5-carboxylic acid(2-hydroxy-ethoxy)-amide
6-(4-bromo-2-chlorophenylamino)-7-fluoro-3-methyl-3H-benzoimidazole-5-carboxylic acid (2-hydroxyethoxy)-amide
6-(4-bromo-2-chlorophenylamino)-7-fluoro-3-methyl-3H-benzoimidazole-5-carboxylic acid(2-hydroxyethoxy)-amide
6-(4-bromo-2chloro-phenylamino)-7-fluoro-3-methyl-3H-benzoimidazole-5-carboxylic acid (2-hydroxy-ethoxy)-amide
分子式C17H15BrClFN4O3 
分子量457.7
InChIInChI=1S/C17H15BrClFN4O3/c1-24-8-21-16-13(24)7-10(17(26)23-27-5-4-25)15(14(16)20)22-12-3-2-9(18)6-11(12)19/h2-3,6-8,22,25H,4-5H2,1H3,(H,23,26)
InChI KeyCYOHGALHFOKKQC-UHFFFAOYSA-N
Isomeric SMILESCCN1C=NC2=C1C=C(C(=C2F)NC3=C(C=C(C=C3)Br)Cl)C(=O)NOCCO
Patent Information
Patent IDTitlePublication Date
CN109438362Substituted benzimidazole compound and composition with compound2019
WO2018/65924INTERMEDIATES OF MITOGEN-ACTIVATED PROTEIN KINASE KINASE (MAP2K OR MEK) INHIBITORS AND PROCESS FOR THEIR PREPARATION2018
US2004/116710N3 alkylated benzimidazole derivatives as MEK inhibitors2004
US2003/232869N3 alkylated benzimidazole derivatives as MEK inhibitors2003

Physical Data

AppearanceWhite or off-white powder.

Spectra

Description (NMR Spectroscopy)Nucleus (NMR Spectroscopy)Solvents (NMR Spectroscopy)Frequency (NMR Spectroscopy), MHz
Solid state NMR, Chemical shifts, Spectrum19F376
1HCD3OD400
19FCD3OD376
1HCD3OD

Route of Synthesis (ROS)

Route of Synthesis (ROS) of Selumetinib CAS# 606143-52-6
Route of Synthesis (ROS) of Selumetinib CAS# 606143-52-6
ConditionsYield
With hydrogenchloride; water In ethanol for 24h;

Experimental Procedure
Hydrochloric acid (14 mL, 1.0 M aqueous solution, 14 mmol) was added to a suspension of 6-(4-bromo-2-chloro- phenylamino)-7-fluoro-3-methyl-3H-benzoimidazole-5-carboyxlic acid (2-vinyloxyethoxy)- amide (2.18 g, 4.50 mmol) in ethanol (50 mL) and the reaction mixture allowed to stir for 24 hours. The reaction mixture was concentrated to dryness by rotary evaporation and the solids partitioned between 3:1 ethyl acetate/tetrahydrofuran and saturated potassium carbonate. The aqueous phase was extracted with 3:1 ethyl acetate/tetrahydrofuran (3x), the combined organics dried (Na2SO4), and concentrated to provide 2.11 g (100%) 6-(4-bromo-2- chlorophenylamino)-7-fluoro-3-methyl-3H-benzoimidazole-5-carboxylic acid (2- hydroxyethoxy)-amide as an off-white solid. MS ESI (+) m/z 457, 459 (M+, Br pattern) detected. 1H NMR (400 MHz, MeOH-&0 δ 8.26 (s, IH), 7.78 (s, IH), 7.57 (d, IH), 7.24 (dd, IH), 6.40 (dd, IH), 3.86 (s, 3H), 3.79 (m, 2H), 3.49 (m, 2H). 19F NMR (376 MHz, MeOH-d4) -133.68 (s).		100%
With hydrogenchloride In ethanol; water at 25 – 30℃; for 24h;

Experimental Procedure
7 Example 7: Preparation of 5-[(4-Bromo-2-chlorophenyl)aminoj-4-fluoro-N-(2- hydroxyethoxy)- 1-methyl- 1H-benzimidazole-6-carboxamide (Selumetinib)
Aqueous hydrochloric acid (iN, 1.2 mL hydrochloric acid in 12 mL deionized water) was added slowly to a solution of 5-[(4-Bromo-2-chlorophenyl)aminoj-N-[2-(ethenyloxy)ethoxyj -4-fluoro- 1-methyl- 1H-benzimidazole-6-carboxamide (1.3 g; obtained from Example 6) in ethanol (30 mL) over a period of 10 minutes and the reaction mixture was stirred at 25°C to 30°C for 24 hours. After completion of the reaction (monitored by TLC), ethanol was concentrated under vacuum. Ethyl acetate: tetrahydrofuran (3:1, 45:15 mL) was added and the organic layer was washed with saturated potassium carbonatesolution (25 mL). The organic layer was separated and the aqueous layer was washed with ethyl acetate: tetrahydrofuran (45: 15 mL) solution. The organic layers were combined and dried over sodium sulphate and then concentrated under vacuum to obtain a crude compound as a brown solid (950 mg). The crude compound was further purified by column chromatography using 2% methanol/dichloromethane as an eluent to obtain thetitle compound.Yield: 70%		70%

Safety and Hazards

Pictogram(s)skullexclamation-markhealth-hazardenvironment
SignalDanger
GHS Hazard StatementsH317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]
H318 (100%): Causes serious eye damage [Danger Serious eye damage/eye irritation]
H361 (100%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]
H373 (100%): May causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]
H411 (100%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]
Precautionary Statement CodesP203, P260, P261, P264+P265, P272, P273, P280, P302+P352, P305+P354+P338, P317, P318, P319, P321, P333+P317, P362+P364, P391, P405, and P501
(The corresponding statement to each P-code can be found at the GHS Classification page.)

Other Data

Transportation
HS Code
StorageUnder the room temperature and away from light
Shelf Life2 years
Market Price
Druglikeness
Lipinski rules component
分子量457.687
logP3.696
HBA5
HBD3
Matching Lipinski Rules4
Veber rules component
Polar Surface Area (PSA)88.41
Rotatable Bond (RotB)7
Matching Veber Rules2
Use Pattern
Selumetinib CAS#: 606143-52-6 is used for the treatment of advanced non-small cell lung cancer (NSCLC). Selumetinib primarily inhibits the growth of various tumors, including melanomas with B-Raf mutations and non-small cell lung cancer (NSCLC) with K-Ras mutations, by regulating the key protein kinase MEK in the Ras-Raf-MEK-ERK pathway. It is mainly employed in the treatment of diseases such as cholangiocarcinoma, colorectal cancer, and NSCLC. Currently, Selumetinib is in phase III clinical trials for the treatment of non-small cell lung cancer.

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Caming Pharmaceutical Limitedhttp://www.caming.com/
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