ChemicalBook >> CAS DataBase List >>2-[3,5-bis(trifluoromethyl)phenyl]-N,2-dimethyl-N-[4-(2-methylphenyl)-6-(4-methylpiperazin-1-yl)pyridin-3-yl]propanamide

2-[3,5-bis(trifluoromethyl)phenyl]-N,2-dimethyl-N-[4-(2-methylphenyl)-6-(4-methylpiperazin-1-yl)pyridin-3-yl]propanamide

2-[3,5-bis(trifluoromethyl)phenyl]-N,2-dimethyl-N-[4-(2-methylphenyl)-6-(4-methylpiperazin-1-yl)pyridin-3-yl]propanamide structure

CAS No.: 290297-26-6

Chemical Name:: 2-[3,5-bis(trifluoromethyl)phenyl]-N,2-dimethyl-N-[4-(2-methylphenyl)-6-(4-methylpiperazin-1-yl)pyridin-3-yl]propanamide

Synonyms: Netupitant;Netupitan;CID6451149;CID-6451149;CID 6451149;Ro 67-31898;Ro 67-31898/000;Netupitant(CID-6451149);NETUPITANT (RO 67-31898);2-[3,5-bis(trifluoromethyl)phenyl]-N,2-dimethyl-N-[4-(2-meth...

CBNumber:: CB71483126

Molecular Formula:: C30H32F6N4O

Molecular Weight:: 578.59

MDL Number:: MFCD25976831

MOL File:: 290297-26-6.mol

MSDS File:: SDS

Last updated:2023-08-14 17:44:59

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2-[3,5-bis(trifluoromethyl)phenyl]-N,2-dimethyl-N-[4-(2-methylphenyl)-6-(4-methylpiperazin-1-yl)pyridin-3-yl]propanamide Properties

Melting point	156.2-160.0 °C
Boiling point	597.4±50.0 °C(Predicted)
Density	1.255
storage temp.	2-8°C
solubility	Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
pka	7.89±0.38(Predicted)
form	Solid
color	White to Off-White
InChIKey	WAXQNWCZJDTGBU-UHFFFAOYSA-N
SMILES	C(N(C)C1=C(C2C=CC=CC=2C)C=C(N2CCN(C)CC2)N=C1)(=O)C(C1C=C(C(F)(F)F)C=C(C(F)(F)F)C=1)(C)C
FDA UNII	7732P08TIR
NCI Drug Dictionary	netupitant

SAFETY

Risk and Safety Statements

Symbol(GHS)

GHS07

Signal word

Warning

Hazard statements

H315-H319

Precautionary statements

P302+P352-P305+P351+P338

NFPA 704

	0
2		0

2-[3,5-bis(trifluoromethyl)phenyl]-N,2-dimethyl-N-[4-(2-methylphenyl)-6-(4-methylpiperazin-1-yl)pyridin-3-yl]propanamide price More Price(42)

Manufacturer	Product number	Product description	CAS number	Packaging	Price	Updated	Buy
Sigma-Aldrich	SML2755	Netupitant ≥98% (HPLC)	290297-26-6	10MG	$97.7	2024-03-01	Buy
Sigma-Aldrich	SML2755	Netupitant ≥98% (HPLC)	290297-26-6	50MG	$395	2024-03-01	Buy
Cayman Chemical	23809	Netupitant ≥98%	290297-26-6	10mg	$89	2024-03-01	Buy
Cayman Chemical	23809	Netupitant ≥98%	290297-26-6	25mg	$167	2024-03-01	Buy
Cayman Chemical	23809	Netupitant ≥98%	290297-26-6	50mg	$267	2024-03-01	Buy

Product number	Packaging	Price	Buy
SML2755	10MG	$97.7	Buy
SML2755	50MG	$395	Buy
23809	10mg	$89	Buy
23809	25mg	$167	Buy
23809	50mg	$267	Buy

2-[3,5-bis(trifluoromethyl)phenyl]-N,2-dimethyl-N-[4-(2-methylphenyl)-6-(4-methylpiperazin-1-yl)pyridin-3-yl]propanamide Chemical Properties,Uses,Production

Description

Netupitant, originally developed by Helsinn Healthcare and later licensed to Eisai, Inc., was approved in the USA in October 2014 for the treatment of chemotherapy-induced nausea and emesis. Akynzeo ® is a fixed-dose combination of the new drug netupitant and the previously-approved 5-HT3 antagonist palonosetron. While palonosetron obtained approval previously for treating nausea and emesis occurring within the first 24 hours (acute phase) after chemotherapy, netupitant provides a synergistic effect with palonosetron, assisting in prevention of nausea and emesis in later stages following chemotherapy (25–120 h after chemotherapy treatment). Several clinical trials showed that this combination of netupitant and palonosetron (Akynzeo ?), in comparison to treatment with palonosetron treatment alone, led to an improved percentage of patients in all phases who did not experience any nausea and emesis after undergoing chemotherapy. Netupitant itself joins the class of selective Neurokinin- 1 (NK1) receptor antagonists which, in addition to their use for treating chemotherapy-induced nausea and emesis, also play an important role as therapies for depression and anxiety.

Description

Netupitant is an insurmountable antagonist of the neurokinin-1 (NK₁) receptor (K_i = 0.95 nM in CHO cells expressing the human recombinant receptor). It is selective for human NK₁ over human NK₂ and NK₃ and rat NK₁ (K_is = >1,500 nM) and over 50 G protein-coupled receptors, monoamine transporters, and ion channels when used in the nanomolar range. Netupitant decreases the maximal response to substance P-induced contractions in isolated guinea pig ileum with long-lasting effects. It also dose-dependently inhibits the substance P-induced scratching, biting, and licking response in mice when used at doses ranging from 1-10 mg/kg and decreases NK agonist-induced foot tapping in gerbils (ID₅₀s = 1.5 mg/kg, i.p., or 0.5 mg/kg, oral). Formulations containing netupitant have been used in the treatment of chemotherapy-induced nausea and vomiting.

Uses

Antiemetic.

Uses

Netupitant is a potent and selective neurokinin-1 receptor (NK1) receptor antagonist. It is achiral and orally active.

Definition

ChEBI: A monocarboxylic acid amide obtained by formal condensation of the carboxy group of 2-[3,5-bis(trifluoromethyl)phenyl]-2-methylpropanoic acid with the secondary amino group of N-methyl-4-(2-methylphenyl)-6-(4-methylpiperazin-1-yl)pyridin 3-amine; an antiemetic used in combination with palonosetron hydrochloride (under the trade name Akynzeo) to treat nausea and vomiting in patients undergoing cancer chemotherapy.

Synthesis

The most likely process-scale synthesis of netupitant begins with 6-chloronicotinic acid (185). From 185, a one-pot 1,4-Grignard addition/oxidation reaction, developed to provide an improved route to NK1 receptor antagonists, was employed for direct installation of the C4-o-tolyl substituent. Using this procedure, treatment of 6-chloronicotinic acid (185) with otolyl magnesium chloride and subsequent oxidation with Mn (OAc)2 in THF/AcOH generated the o-tolyl nicotinic acid intermediate 187 in 51% overall yield. From this intermediate, a one-pot amide formation could be realized in high yield by conversion of the acid to the corresponding acyl chloride and addition of NH4OH (95% yield). Chloride displacement with 1-methyl piperazine under heating conditions provided intermediate 189 in 95% yield. Employing Hoffman reaction conditions originally reported by Senanayake,171 rearrangement of amide 189 with NBS/NaOMe/ MeOH enabled formation of carbamate 190 in quantitative yield. Reduction of the carbamate with Red-Al provided the desired mono-methylated amine. To access the final drug target, acylation of the intermediate methyl amine with 2-(3,5-bis(trifluoromethyl) phenyl)-2-methylpropanoyl chloride (191) provided the final drug netupitant (XXII) in 81% yield. In this case, due to the cost of 193, the acid precursor to 191, and starting materials previously reported for generating 191/193, as well as issues with isolation of pure intermediates on scale, a novel route to 191 and 193 was also developed during this synthesis, beginning with the inexpensive and readily available bromide 192. This 2-step synthesis of 193 includes Grignard reagent formation, quenching with acetone to yield the intermediary tertiary alcohol, and subsequent carbonylation (TfOH, H2O, CO then NaOH/H2O) to provide 2-(3,5-bis(trifluoromethyl)-phenyl)-2- methylpropanoic acid 193. Finally, conversion of acid 193 to the acyl chloride with oxalyl chloride in DCM provided the necessary acyl chloride 191 in quantitative yield (86% purity).

Synthesis_290297-26-6

2-[3,5-bis(trifluoromethyl)phenyl]-N,2-dimethyl-N-[4-(2-methylphenyl)-6-(4-methylpiperazin-1-yl)pyridin-3-yl]propanamide synthesis

Synthesis of 2-[3,5-bis(trifluoromethyl)phenyl]-N,2-dimethyl-N-[4-(2-methylphenyl)-6-(4-methylpiperazin-1-yl)pyridin-3-yl]propanamide from 3-PYRIDINAMINE, N-METHYL-4-(2-METHYLPHENYL)-6-(4-METHYL-1-PIPERAZINYL)- and 2-(3,5-bis-trifluoromethylphenyl)-2-methyl-propionyl chloride

2-[3,5-bis(trifluoromethyl)phenyl]-N,2-dimethyl-N-[4-(2-methylphenyl)-6-(4-methylpiperazin-1-yl)pyridin-3-yl]propanamide Preparation Products And Raw materials

Raw materials

N-[4-iodo-6-(4-methyl-piperazin-1-yl)-pyridin-3-yl]-2,2-dimethyl-propionamide Benzeneacetamide, N-[6-chloro-4-(2-methylphenyl)-3-pyridinyl]-N,α,α-trimethyl-3,5-bis(trifluoromethyl)- 6-CHLORO-4-O-TOLYL-NICOTINAMIDE 6-CHLORO-4-O-TOLYL-NICOTINIC ACID N-(6-(4-Methylpiperazin-1-yl)pyridin-3-yl)pivalaMide

2-(3,5-bis-trifluoromethylphenyl)-2-methyl-propionyl chloride N-tert-butyl-6-chloro-4-(o-tolyl)nicotinamide 3-PYRIDINAMINE, N-METHYL-4-(2-METHYLPHENYL)-6-(4-METHYL-1-PIPERAZINYL)- 2-(4-Methylpiperazin-1-yl)-5-nitropyridine Methyl (6-(4-Methylpiperazin-1-yl)-4-(o-tolyl)pyridin-3-yl)carbaMate

3-PYRIDINECARBOXAMIDE, 4-(2-METHYLPHENYL)-6-(4-METHYL-1-PIPERAZINYL)- 2-(3,5-bis(trifluoroMethyl)phenyl)-2-Methyl propanoic acid 2-Chloro-5-nitropyridine

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Preparation Products

2-[3,5-bis(trifluoromethyl)phenyl]-N,2-dimethyl-N-[4-(2-methylphenyl)-6-(4-methylpiperazin-1-yl)pyridin-3-yl]propanamide Suppliers

Global( 191)Suppliers

Supplier	Tel	Email	Country	ProdList	Advantage
Aceschem Inc.	+1-817863-6948 +1-（817）863-6948	sales@aceschem.com	United States	19639	58
shandong perfect biotechnology co.ltd	+86-53169958659; +8618596095638	sales@sdperfect.com	China	294	58
Beijing Cooperate Pharmaceutical Co.,Ltd	010-60279497	sales01@cooperate-pharm.com	CHINA	1811	55
Henan Tianfu Chemical Co.,Ltd.	+86-0371-55170693 +86-19937530512	info@tianfuchem.com	China	21691	55
ATK CHEMICAL COMPANY LIMITED	+undefined-21-51877795	ivan@atkchemical.com	China	32480	60
TianYuan Pharmaceutical CO.,LTD	+86-755-23284190 13684996853	sales@tianpharm.com	CHINA	304	58
BOC Sciences	+1-631-485-4226	inquiry@bocsci.com	United States	19553	58
CONIER CHEM AND PHARMA LIMITED	+8618523575427	sales@conier.com	China	49390	58
career henan chemical co	+86-0371-86658258 15093356674;	factory@coreychem.com	China	29826	58
WinWin Chemical CO., Limited	+86-0577-64498589 +8615325081899	sales@win-winchemical.com	China	13854	58

Supplier	Advantage
Aceschem Inc.	58
shandong perfect biotechnology co.ltd	58
Beijing Cooperate Pharmaceutical Co.,Ltd	55
Henan Tianfu Chemical Co.,Ltd.	55
ATK CHEMICAL COMPANY LIMITED	60
TianYuan Pharmaceutical CO.,LTD	58
BOC Sciences	58
CONIER CHEM AND PHARMA LIMITED	58
career henan chemical co	58
WinWin Chemical CO., Limited	58

View Lastest Price from 2-[3,5-bis(trifluoromethyl)phenyl]-N,2-dimethyl-N-[4-(2-methylphenyl)-6-(4-methylpiperazin-1-yl)pyridin-3-yl]propanamide manufacturers

Update time	Product	Price	Min. Order	Purity	Supply Ability	Manufacturer
2024-03-12	Netupitant 290297-26-6	US $0.00 / g	1g	98% HPLC	100kg	shandong perfect biotechnology co.ltd
2023-03-06	Netupitant 290297-26-6	US $77.60 / KG	1KG	99%	5000kg	Hebei Guanlang Biotechnology Co,.LTD
2021-11-27	2-[3,5-bis(trifluoromethyl)phenyl]-N,2-dimethyl-N-[4-(2-methylphenyl)-6-(4-methylpiperazin-1-yl)pyridin-3-yl]propanamide 290297-26-6	US $44.00 / g	100g	99.99%	5ton/Month	Qiuxian Baitai New Material Co., LTD

Netupitant
290297-26-6
US $0.00 / g
98% HPLC
shandong perfect biotechnology co.ltd

Netupitant
290297-26-6
US $77.60 / KG
99%
Hebei Guanlang Biotechnology Co,.LTD

2-[3,5-bis(trifluoromethyl)phenyl]-N,2-dimethyl-N-[4-(2-methylphenyl)-6-(4-methylpiperazin-1-yl)pyridin-3-yl]propanamide
290297-26-6
US $44.00 / g
99.99%
Qiuxian Baitai New Material Co., LTD

2-[3,5-bis(trifluoromethyl)phenyl]-N,2-dimethyl-N-[4-(2-methylphenyl)-6-(4-methylpiperazin-1-yl)pyridin-3-yl]propanamide Spectrum

2-[3,5-bis(trifluoromethyl)phenyl]-N,2-dimethyl-N-[4-(2-methylphenyl)-6-(4-methylpiperazin-1-yl)pyridin-3-yl]propanamide(290297-26-6)¹HNMR

290297-26-6(2-[3,5-bis(trifluoromethyl)phenyl]-N,2-dimethyl-N-[4-(2-methylphenyl)-6-(4-methylpiperazin-1-yl)pyridin-3-yl]propanamide)Related Search:

Methyl (6-(4-Methylpiperazin-1-yl)-4-(o-tolyl)pyridin-3-yl)carbaMate 3-PYRIDINAMINE, N-METHYL-4-(2-METHYLPHENYL)-6-(4-METHYL-1-PIPERAZINYL)- 3-PYRIDINECARBOXAMIDE, 4-(2-METHYLPHENYL)-6-(4-METHYL-1-PIPERAZINYL)- N-tert-butyl-6-chloro-4-(o-tolyl)nicotinamide Sulfachoropyrazine sodium

Pyrazinamide Indole Furan Pyridoxine Pyrazole

Oxazole Pyrrole Pyridine

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2-[3,5-Bis(trifluoromethyl)phenyl]-N-[6-(4-methylpiperazin-1-yl)-4-(o-tolyl)pyridin-3-yl]-N-methylisobutyramide 2-[3,5-bis(trifluoromethyl)phenyl]-N,2-dimethyl-N-[4-(2-methylphenyl)-6-(4-methylpiperazin-1-yl)pyridin-3-yl]propanamide Ro 67-31898/000 2-(3,5-bis(trifluoroMethyl)phenyl)-N,2- diMethyl-N-(6-(4-Methylpiperazin-1-yl)-4- o-tolylpyridin-3-yl)propanaMide BenzeneacetaMide, N,a,a-triMethyl-N-[4-(2-Methylphenyl)-6-(4-Methyl-1-piperazinyl)-3-pyridinyl]-3,5-bis(trifluoroMethyl)- 2-[3,5-bis(trifluoromethyl)phenyl]-N,2-dimethyl-N-[4-(2-methylphenyl)-6-(4-methylpiperazin-1-yl)pyridin-3- Ro 67-31898 Netupitan CID 6451149 CID6451149 CID-6451149 Netupitant(CID-6451149) 2-[3,5-Bis(trifluoromethyl)phenyl]-N,2-dimethyl-N-[4-(2-methylphenyl)-6-(4-methylpiperazin-1-y NETUPITANT (RO 67-31898) Benzeneacetamide, N,α,α-trimethyl-N-[4-(2-methylphenyl)-6-(4-methyl-1-piperazinyl)-3-pyridinyl]-3,5-bis(trifluoromethyl)- 2-[3,5-bis(trifluoromethyl)phenyl]-N,2-dimethyl-N-[4-(2-meth... NetupitantQ: What is Netupitant Q: What is the CAS Number of Netupitant Q: What is the storage condition of Netupitant Q: What are the applications of Netupitant Netupitant 290297-26-6 290297-36-6 C30H32F6N4O