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Sorafenib
Cas No: 284461-73-0
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Sorafenib tosylate,284461-73-0
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Sorafenib
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284461-73-0 Usage

Chemical Properties

Light Yellow Solid

Originator

Bayer/Onyx (Germany)

Brand name

Nexavar (Bayer HealthCare); Xarelto (Bayer HealthCare).

Uses

Multiple kinase inhibitor targeting both RAF kinase and receptor tyrosine kinases that promote angiogensis. Antineoplastic.

References

El-Serag HB, Rudolph KL. Hepatocellular carcinoma: epidemiology and molecular carcinogenesis. Gastroenterology 2007 Jun; 132 (7): 2557-76 Adnane L, Trail PA, Taylor I, et al. Sorafenib (BAY 439006, Nexavar), a dual-action inhibitor that targets RAF/MEK/ERK pathway in tumor cells and tyrosine kinases VEGFR/PDGFR in tumor vasculature. Methods Enzymol 2005; 407: 597-612 Wilhelm S, Carter C, Lynch M, et al. Discovery and development of sorafenib: a multikinase inhibitor for treating cancer. Nat Rev Drug Discov 2006 Oct; 5 (10): 835-44 Wilhelm SM, Carter C, Tang LY, et al. BAY 43-9006 exhibits broad spectrum oral antitumor activity and targets the RAF/MEK/ERK pathway and receptor tyrosine kinases involved in tumor progression and angiogenesis. Cancer Res 2004 Oct 1; 64 (19): 7099-109 Yu C, Bruzek LM, Meng XW, et al. The role of Mcl-1 downregulation in the proapoptotic activity of the multikinase inhibitor BAY 43-9006. Oncogene 2005;24:6861-9 Himmelsbach K, Sauter D, Baumert TF, et al. New aspects of an anti-tumour drug: sorafenib efficiently inhibits HCV replication. Gut 2009;58:1644-53 Molhoek KR, McSkimming CC, Olson WC, et al. Apoptosis of CD4(+) CD25(high) T cells in response to Sirolimus requires activation of T cell receptor and is modulated by IL-2. Cancer Immunol Immunother 2009;58:867-76 Strumberg D, Richly H, Hilger RA, et al. Phase I clinical and pharmacokinetic study of the Novel Raf kinase and vascular endothelial growth factor receptor inhibitor BAY 43-9006 in patients with advanced refractory solid tumors. J Clin Oncol 2005;23:965-72 Clinical Pharmacology and Biopharmaceutics NDA Review for Sorafenib Tosylate (NDA 21 923), F.C.F.D.E.A. RESEARCH, Editor, 2005 BAY 43-9006 (sorafenib) Investigator’s Brochure. Bayer Healthcare AG,Version 10.0, July 1, 2009 European Medicines Agency. Sorafenib (Nexavar): summary of product characteristics [online]. Blanchet B, Billemont B, Barete S, et al. Toxicity of sorafenib: clinical and molecular aspects. Expert Opin Drug Saf 2010;9:275-87 https://www.drugs.com/cdi/sorafenib.html

Uses

Sorafenib, an orally active potent multi-kinases inhibitor,was approved in the U.S. for the treatment of advanced renalcell carcinoma. The drug targets both tumor cell proliferationand tumor angiogenesis kinases that include RAF,VEGFR-2, VEGFR-3, PDGFR-??, KIT and FLT-3. Sorafenibis being jointly developed by Bayer and Onyx in phase IIItrials as a single agent for the treatment of advanced hepato-cellular carcinoma and in combination with carboplatin andpaclitaxel in patients with advanced metastatic melanoma.Phase II trials in combination with doxorubicin for thetreatment of advanced hepatocellular carcinoma are alsounder investigation. Additional phase II trials are ongoingfor non-small cell lung cancer (NSCLC) and in postmenopausalwomen with estrogen receptor and/or progesteronereceptor-positive metastatic breast cancer. In addition, theNational Cancer Institute (NCI) is evaluating the compoundboth as a single therapy agent and in combination with otheroncology agents in phase II trials for several cancer indications.

Indications

It is indicated for the treatment of hepatocellular carcinoma and the treatment of advanced renal cell carcinoma (primary kidney cancer).

Uses

A potent RAF kinase inhibitor. Antineoplastic

Uses

Sorafenib Tosylate (Bay 43-9006) is a multikinase inhibitor of Raf-1, B-Raf and VEGFR-2 with IC50 of 6 nM, 22 nM and 90 nM, respectively - See more at: http://www.selleckchem.com/products/Sorafenib-Tosylate.html#sthash.BjHEmCf3.dpuf

Side effects

The most common adverse reactions (20%), considered to be related to sorafenib, in patients with HCC or RCC are fatigue, weight loss, rash/desquamation, hand-foot skin reaction, alopecia, diarrhea, anorexia, nausea and abdominal pain [12]. Across all tumor types, common side effects (> 10%) include hypertension (9 -13%, grade 4: < 1%; onset: ~ 3 weeks), fatigue (37 -46%), sensory neuropathy (13%), pain (11%), rash/desquamation (19 -40%; grade 3: 1%), handfoot syndrome (21 -30%; grade 3: 6 -8%), alopecia (14 -27%), pruritis (14 -19%), dry skin (10 -11%), hypoalbuminemia (59%), hypophosphatemia (35 -45%; grade 3: 11 -13%; grade 4: < 1%), diarrhea (43 -55%; grade 3: 2 -10%; grade 4: < 1%), lipase increased (40 -41%, usually transient), amylase increased (30 -34, usually transient), abdominal pain (11 -31%), weight loss (10 -30%), anorexia (16 -29%), nausea (23 -24%), vomiting (15 -16%), constipation (14 -15%), muscle pain, weakness, dyspnea (14%), cough (13%) and hemorrhage (15 -18%; grade 3: 2 -3%; grade 4: 2%). Laboratory abnormalities attributable to sorafenib use are also seen and include lymphopenia (23 -47%; grades 3/4: 13%), thrombocytopenia (12 -46%; grades 3/4: 1 -4%), international normalized ration (INR) increased (42%), neutropenia (18%; grades 3/4: 5%), leucopenia, liver dysfunction (11%; grade 3: 2%; grade 4: 1%). Less frequent side effects (> 1 -10) include cardiac ischemia/infarction (3%), flushing, headache (10%), depression, fever, acne, exfoliative dermatitis, decreased appetite, dyspepsia, dysphagia, esophageal varices bleeding (2%), glossodynia, mucositis, stomatitis, xerostomia, erectile dysfunction, anemia, transaminases increased (transient), joint pain (10%), arthralgia, myalgia, hoarseness and flu-like syndrome. Rare (< 1%) side effects of sorafenib include acute renal failure, alkaline phosphatase increased, arrhythmia, bilirubin increased, bone pain, cardiac failure, cerebral hemorrhage, congestive heart failure, dehydration, eczema, epistaxis, erythema multiforme, folliculitis, gastritis, gastrointestinal hemorrhage, gastrointestinal perforation, gastrointestinal reflux, gynecomastia, hypersensitivity (skin reaction, urticaria), hypertensive crisis, hyponatremia, hypothyroidism, infection, jaundice, myocardial infarction (MI), mouth pain, myocardial ischemia, pancreatitis, pleural effusion, preeclampsialike syndrome (reversible hypertension and proteinuria), renal failure, respiratory hemorrhage, reversible posterior leukoencephalopathy syndrome (RPLS), rhinorrhea, skin cancer (squamous cell/keratoacanthomas), thromboembolism, tinnitus, transient ischemic attack, tumor lysis syndrome, tumor pain and voice alteration.

Indications

Sorafenib (Nexavar(R), Bayer) was the first approved inhibitor targeting the vascular endothelial growth factor (VEGF) family kinases, which include VEGFR1, VEGR2, and VEGFR3. Sorafenib was originally approved for the treatment of renal cell carcinoma (RCC) in 2005, hepatocellular carcinoma in 2007, and locally recurrent or metastatic thyroid carcinoma refractory to radioactive iodine treatment in 2013. Six other approved inhibitors with VEGFRs as the main targets are sunitinib (Sutent(R), Pfizer) for RCC, soft tissue sarcoma, thyroid cancer,metastatic pancreatic tumors, gastrointestinal stromal tumor, and several other types of carcinomas; pazopanib (Votrient(R), GlaxoSmithKline) for RCC, soft tissue sarcoma, and thyroid cancer; axitinib (Inlyta(R), Pfizer) for RCC,thyroid cancer, and aplastic anemia, as well as T315I-mutant Bcr–Abl1-driven leukemia; regorafenib (Stivarga(R), Bayer) for gastrointestinal stromal tumors and colorectal cancer; nintedanib (Ofev(R), Boehringer Ingelheim) for the non-oncological indication of idiopathic pulmonary fibrosis; and lenvatinib (Lenvima(R), Eisai Inc.) for RCC and different types of thyroid cancers. Sunitinib, pazopanib, and lenvatinib bind to the “DFG-in”conformation of VEGFRs, while axitinib, regorafenib, and nintedanib bind to inactive VEGFRs adopting the “DFG-out”conformation.

Description

Sorafenib is a small molecular inhibitor of several kinases involved in tumor angiogenesis and proliferation, including, but not limited to, Raf (IC50=12nM for Raf-1), VEGFR (IC50=90nM for VEGFR-2 and IC50=12nM for VEGFR-3), and platelet derived growth factor receptor (IC50=57nM for PDGFR-b). Specifically, sorafenib blocks tumor progression by inhibiting cellular proliferation that is dependent on activation of the MAPK pathway (Raf) and/or inhibiting tumor angiogenesis through VEGFR and/or PDGFR. While it may be effective in the treatment of a variety of tumors, the first approvable indication is for renal cell carcinoma. Overall, the drug appears to be well tolerated by the majority of patients at the 400 mg b.i.d. continuous dosing. As an inhibitor of multiple kinases vital for tumor progression, sorafenib may possess wide-spectrum antitumor properties and may emerge as an effective weapon against a variety of solid tumors.

Overview

Sorafenib tosylate is the tosylate form of sorafenib, which is a drug approved for the treatment of hepatocellular carcinoma and the treatment of advanced renal cell carcinoma (primary kidney cancer). Hepatocellular carcinoma accounts for the vast majority of primary liver cancers (85–90%). [1] Approximately 70–90% of all hepatocellular cancer cases occur in patients with chronic liver disease and cirrhosis, with the main causes of cirrhosis including hepatitis B, hepatitis C and alcoholic liver disease.[1] Sorafenib is an oral receptor tyrosine kinase inhibitor that inhibits Raf serine/threonine kinases and receptor tyrosine kinases (vascular endothelial growth factor receptors 1, 2, 3 and platelet-derived growth factor-b, Flt-3 and c-kit) that are implicated in tumorigenesis and tumor progression. Figure 1 the chemical structure of sorafenib;

Mechanism of action

The bi-aryl urea sorafenib is an oral multikinase inhibitor that inhibits both cell surface tyrosine kinase receptors and downstream intracellular serine/threonine kinases in the Ras/MAPK cascade.[2-4] Receptor tyrosine kinases inhibited by sorafenib include vascular endothelial growth factor receptor (VEGFR)-1, VEGFR-2, VEGFR-3, platelet-derived growth factor receptor (PDGFR)-b, c-KIT, FMS-like tyrosine kinase 3 (FLT-3) and RET. Intracellular Raf serine/threonine kinase isoforms inhibited by sorafenib include Raf-1 (or C-Raf), wild-type B-Raf and mutant B-Raf.[3, 4] These kinases are involved in tumour cell proliferation and tumour angiogenesis.[3, 4] The antiproliferative activity of sorafenib is variable in different tumor types and largely depends on the oncogenic signaling pathways that mediate tumor proliferation. Sorafenib has also been shown to induce apoptosis in several tumor cell lines. Although the mechanism through which sorafenib induces apoptosis is not fully elucidated and may vary between cell lines, a commonly observed theme is the inhibition of phosphorylation of the initiation factor eIF4E and loss of the antiapoptotic protein myeloid cell leukemia-1 (MCL-1)[5]. Recently, sorafenib was shown to inhibit hepatitis C viral replication in vitro[6], and in vitro studies have also shown some direct effects on immune cells [7]. Whether these effects

Uses

Sorafenib Tosylate (Bay 43-9006, Nexavar) is a small molecular inhibitor of VEGFR, PDGFR, c-Raf and B-Raf with IC50s of 18 nM, 10 nM, 3 nM and 15 nM, respectively.

Chemical Synthesis

An improved, four-step synthesis in 63% overall yield was published recently and is illustrated in the scheme. Picolinic acid (127) was heated with Vilsmeier reagent for 16 hr to give 128 in 89% yield as an off-white solid. The acid chloride 128 was treated with methylamine in methanol at low temperature to give amide 129 in 88% yield as paleyellow crystals after its crystallization from ethyl acetate.4-Aminophenol anion was generated under a basic condition and compound 129 was added to the anion solution to give corresponding addition compound 131 in 87% yield. For an unknown reason, potassium carbonate used in the reaction increased the reaction rate significantly. Finally, compound 131 was condensed with isocyanate 132 in methylene chloride to give sorafenib (XVIII) in 92% yield as a white solid.
InChI:InChI=1/C21H16ClF3N4O3.C7H8O3S/c1-26-19(30)18-11-15(8-9-27-18)32-14-5-2-12(3-6-14)28-20(31)29-13-4-7-17(22)16(10-13)21(23,24)25;1-6-2-4-7(5-3-6)11(8,9)10/h2-11H,1H3,(H,26,30)(H2,28,29,31);2-5H,1H3,(H,8,9,10)

284461-73-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name sorafenib

1.2 Other means of identification

Product number -
Other names Nexavar

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:284461-73-0 SDS

284461-73-0Synthetic route

4-chloro-3-trifluoromethylphenylurea
343247-69-8

4-chloro-3-trifluoromethylphenylurea

[4-(4-bromophenoxy)(2-pyridyl)]-N-methylcarboxamide
1154243-75-0

[4-(4-bromophenoxy)(2-pyridyl)]-N-methylcarboxamide

sorafenib
284461-73-0

sorafenib

Conditions
ConditionsYield
Stage #1: [4-(4-bromophenoxy)(2-pyridyl)]-N-methylcarboxamide With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 20℃; for 0.5h;
Stage #2: 4-chloro-3-trifluoromethylphenylurea In 1,4-dioxane at 80 - 100℃; for 1h; Solvent; Reagent/catalyst;
97.9%
With t-BuBrettPhos; palladium diacetate; caesium carbonate In tetrahydrofuran; water at 75℃; for 5h; Inert atmosphere;206 mg
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

(4-chloro-3-trifluoromethyl aniline)carboxylic acid allyl ester

(4-chloro-3-trifluoromethyl aniline)carboxylic acid allyl ester

sorafenib
284461-73-0

sorafenib

Conditions
ConditionsYield
With 1-Methylpyrrolidine In dichloromethane at 30℃; for 24h; Solvent; Temperature;97.6%
4-[ ({[4-chloro-3-(trifluoromethyl)phenyl]amino}carbonyl)amino]phenol
1129683-83-5

4-[ ({[4-chloro-3-(trifluoromethyl)phenyl]amino}carbonyl)amino]phenol

4-bromo-pyridine-2-carboxylic acid methyl amide
1209459-88-0

4-bromo-pyridine-2-carboxylic acid methyl amide

sorafenib
284461-73-0

sorafenib

Conditions
ConditionsYield
Stage #1: 4-[ ({[4-chloro-3-(trifluoromethyl)phenyl]amino}carbonyl)amino]phenol With 2,2,6,6-tetramethylheptane-3,5-dione; caesium carbonate; copper(l) chloride In 1-methyl-pyrrolidin-2-one at 50 - 60℃; for 0.5h;
Stage #2: 4-bromo-pyridine-2-carboxylic acid methyl amide In 1-methyl-pyrrolidin-2-one for 2h; Reagent/catalyst; Reflux;
96.7%
4-hydroxy-N-methylpyridine-2-carboxamide
611226-36-9, 1061231-84-2

4-hydroxy-N-methylpyridine-2-carboxamide

4-[ ({[4-chloro-3-(trifluoromethyl)phenyl]amino}carbonyl)amino]phenol
1129683-83-5

4-[ ({[4-chloro-3-(trifluoromethyl)phenyl]amino}carbonyl)amino]phenol

sorafenib
284461-73-0

sorafenib

Conditions
ConditionsYield
at 132℃;96.3%
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

4-chloro-3-(trifluoromethyl)phenyl isocyanate
327-78-6

4-chloro-3-(trifluoromethyl)phenyl isocyanate

sorafenib
284461-73-0

sorafenib

Conditions
ConditionsYield
With zirconia grinding balls In acetonitrile for 4h; Milling;96%
In ethyl acetate at 20 - 30℃; Large scale;94.2%
In dichloromethane93%
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

N-[4-chloro-3-(trifluoromethyl)phenyl]-1H-imidazole-1-carboxamide
1187086-96-9

N-[4-chloro-3-(trifluoromethyl)phenyl]-1H-imidazole-1-carboxamide

sorafenib
284461-73-0

sorafenib

Conditions
ConditionsYield
In chlorobenzene at 70 - 75℃; for 0.25h; Product distribution / selectivity;95%
In ethyl acetate at 20 - 50℃; for 2.75h;77%
With potassium carbonate In dichloromethane for 8h; Milling;72%
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

4-chloro-3-(trifluoromethyl)benzoic acid
1737-36-6

4-chloro-3-(trifluoromethyl)benzoic acid

2,2,2,-trichloroethoxycarbonyl azide

2,2,2,-trichloroethoxycarbonyl azide

sorafenib
284461-73-0

sorafenib

Conditions
ConditionsYield
Stage #1: 4-chloro-3-(trifluoromethyl)benzoic acid; 2,2,2,-trichloroethoxycarbonyl azide With dmap; copper diacetate In dimethyl sulfoxide at 100℃; for 6h; Curtius Rearrangement; Inert atmosphere;
Stage #2: 4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 100℃; for 24h; Inert atmosphere;
93%
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

4-chloro-3-trifluoromethyl-aniline
320-51-4

4-chloro-3-trifluoromethyl-aniline

1,1'-carbonyldiimidazole
530-62-1

1,1'-carbonyldiimidazole

sorafenib
284461-73-0

sorafenib

Conditions
ConditionsYield
Stage #1: 4-chloro-3-trifluoromethyl-aniline; 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 16h; Inert atmosphere;
Stage #2: 4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide In dichloromethane Inert atmosphere;
91%
Stage #1: 4-chloro-3-trifluoromethyl-aniline; 1,1'-carbonyldiimidazole In dichloromethane at 25 - 35℃; for 18h;
Stage #2: 4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide In dichloromethane at 25 - 35℃; for 48.75h;
90 g
4-amino-phenol
123-30-8

4-amino-phenol

4-chloro-3-(trifluoromethyl)phenyl isocyanate
327-78-6

4-chloro-3-(trifluoromethyl)phenyl isocyanate

4-chloro-N-methylpicolinamide
220000-87-3

4-chloro-N-methylpicolinamide

sorafenib
284461-73-0

sorafenib

Conditions
ConditionsYield
Stage #1: 4-amino-phenol; 4-chloro-3-(trifluoromethyl)phenyl isocyanate; 4-chloro-N-methylpicolinamide In N,N-dimethyl-formamide at 20℃; for 2h;
Stage #2: With potassium tert-butylate In N,N-dimethyl-formamide at 60 - 80℃; Solvent; Reagent/catalyst; Temperature;
90.6%
4-[ ({[4-chloro-3-(trifluoromethyl)phenyl]amino}carbonyl)amino]phenol
1129683-83-5

4-[ ({[4-chloro-3-(trifluoromethyl)phenyl]amino}carbonyl)amino]phenol

4-chloro-N-methylpicolinamide
220000-87-3

4-chloro-N-methylpicolinamide

sorafenib
284461-73-0

sorafenib

Conditions
ConditionsYield
With potassium carbonate In toluene Heating;90%
With tetrabutylammomium bromide; potassium iodide; potassium hydroxide In tetrahydrofuran at 80℃; for 10h; Solvent; Reagent/catalyst;89.4%
Stage #1: 4-[ ({[4-chloro-3-(trifluoromethyl)phenyl]amino}carbonyl)amino]phenol With potassium tert-butylate In N,N-dimethyl-formamide for 2h;
Stage #2: 4-chloro-N-methylpicolinamide With potassium carbonate at 80℃; for 6h;
50%
4-(2-methylcarbamoyl-pyridin-4-yloxy)-benzoic acid
827025-43-4

4-(2-methylcarbamoyl-pyridin-4-yloxy)-benzoic acid

4-chloro-3-trifluoromethyl-aniline
320-51-4

4-chloro-3-trifluoromethyl-aniline

sorafenib
284461-73-0

sorafenib

Conditions
ConditionsYield
With diphenyl phosphoryl azide; triethylamine In water at 30 - 100℃;90%
N-[4-chloro-3-(trifluoromethyl)phenyl]-1H-imidazole-1-carboxamide
1187086-96-9

N-[4-chloro-3-(trifluoromethyl)phenyl]-1H-imidazole-1-carboxamide

4-amino-phenol
123-30-8

4-amino-phenol

4-chloro-N-methylpicolinamide
220000-87-3

4-chloro-N-methylpicolinamide

sorafenib
284461-73-0

sorafenib

Conditions
ConditionsYield
Stage #1: N-[4-chloro-3-(trifluoromethyl)phenyl]-1H-imidazole-1-carboxamide; 4-amino-phenol; 4-chloro-N-methylpicolinamide In N,N-dimethyl-formamide at 20℃; for 3h;
Stage #2: With potassium tert-butylate In N,N-dimethyl-formamide at 60 - 80℃;
88.5%
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

4-chloro-3-(trifluoromethyl)benzoic acid
1737-36-6

4-chloro-3-(trifluoromethyl)benzoic acid

sorafenib
284461-73-0

sorafenib

Conditions
ConditionsYield
With diphenyl phosphoryl azide; triethylamine In water at 30 - 100℃;88%
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

3-(4-chloro-3-(trifluoromethyl)phenyl)-1,4,2-dioxazol-5-one

3-(4-chloro-3-(trifluoromethyl)phenyl)-1,4,2-dioxazol-5-one

sorafenib
284461-73-0

sorafenib

Conditions
ConditionsYield
With sodium acetate In methanol at 60℃; for 2h;86%
N-[4-chloro-3-(trifluoromethyl)phenyl]carbamoyl chloride
348-91-4

N-[4-chloro-3-(trifluoromethyl)phenyl]carbamoyl chloride

4-amino-phenol
123-30-8

4-amino-phenol

4-chloro-N-methylpicolinamide
220000-87-3

4-chloro-N-methylpicolinamide

sorafenib
284461-73-0

sorafenib

Conditions
ConditionsYield
Stage #1: N-[4-chloro-3-(trifluoromethyl)phenyl]carbamoyl chloride; 4-amino-phenol; 4-chloro-N-methylpicolinamide In N,N-dimethyl-formamide at 20℃; for 2h;
Stage #2: With potassium tert-butylate In N,N-dimethyl-formamide at 60 - 80℃;
85.5%
4-amino-phenol
123-30-8

4-amino-phenol

(4-chloro-3-trifluoromethylphenyl)carbamic acid phenyl ester
871555-75-8

(4-chloro-3-trifluoromethylphenyl)carbamic acid phenyl ester

4-chloro-N-methylpicolinamide
220000-87-3

4-chloro-N-methylpicolinamide

sorafenib
284461-73-0

sorafenib

Conditions
ConditionsYield
Stage #1: 4-amino-phenol; (4-chloro-3-trifluoromethylphenyl)carbamic acid phenyl ester; 4-chloro-N-methylpicolinamide In N,N-dimethyl-formamide at 20℃; for 3h;
Stage #2: With potassium tert-butylate In N,N-dimethyl-formamide at 60 - 80℃;
85.4%
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

C7H3ClF3NO

C7H3ClF3NO

sorafenib
284461-73-0

sorafenib

Conditions
ConditionsYield
In dichloromethane at 0℃; for 0.25h; Inert atmosphere;85%
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

2,2,2-trichloroethyl (4-chloro-3-(trifluoromethyl)phenyl)carbamate

2,2,2-trichloroethyl (4-chloro-3-(trifluoromethyl)phenyl)carbamate

sorafenib
284461-73-0

sorafenib

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide; acetonitrile at 100℃; for 24h; Schlenk technique; Sealed tube; Inert atmosphere;80%
4-[4-[[[[4-chloro-3-(trifluoromethyl)phenyl]amino]carbonyl]amino]phenoxy]-2-pyridinecarboxylic acid
1012058-78-4

4-[4-[[[[4-chloro-3-(trifluoromethyl)phenyl]amino]carbonyl]amino]phenoxy]-2-pyridinecarboxylic acid

methylamine hydrochloride
593-51-1

methylamine hydrochloride

sorafenib
284461-73-0

sorafenib

Conditions
ConditionsYield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In N,N-dimethyl-formamide at 20℃; for 3h; Inert atmosphere;63.2%
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

(4-chloro-3-trifluoromethylphenyl)carbamic acid phenyl ester
871555-75-8

(4-chloro-3-trifluoromethylphenyl)carbamic acid phenyl ester

sorafenib
284461-73-0

sorafenib

Conditions
ConditionsYield
With pyridine at 80℃; for 3h;48.2%
In N,N-dimethyl-formamide at 40 - 45℃; for 2 - 3h; Product distribution / selectivity;
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 40 - 45℃;
sorafenib tosylate

sorafenib tosylate

sorafenib
284461-73-0

sorafenib

Conditions
ConditionsYield
at 200℃;
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

4-chloro-3-trifluoromethylphenylurea
343247-69-8

4-chloro-3-trifluoromethylphenylurea

sorafenib
284461-73-0

sorafenib

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 110 - 120℃; for 12 - 18h; Product distribution / selectivity;
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 110 - 120℃;
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

1-(4-chloro-3-(trifluoromethyl)phenyl)-3-hydroxyurea
1129683-96-0

1-(4-chloro-3-(trifluoromethyl)phenyl)-3-hydroxyurea

sorafenib
284461-73-0

sorafenib

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 125℃; for 96h; Product distribution / selectivity;
With triethylamine In N,N-dimethyl-formamide at 125℃; for 96h;
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

2,2,2-trichloro-N-(4-chloro-3-(trifluoromethyl)phenyl)acetamide
13692-04-1

2,2,2-trichloro-N-(4-chloro-3-(trifluoromethyl)phenyl)acetamide

sorafenib
284461-73-0

sorafenib

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide for 24h; Product distribution / selectivity; Heating / reflux;
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide for 24h; Reflux;
N-methyl-4-(4-ureidophenoxy)picolinamide
1129683-88-0

N-methyl-4-(4-ureidophenoxy)picolinamide

4-chloro-3-trifluoromethyl-aniline
320-51-4

4-chloro-3-trifluoromethyl-aniline

sorafenib
284461-73-0

sorafenib

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide for 24h; Product distribution / selectivity; Heating / reflux;
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide for 24h; Reflux;
phenyl 4-(2-(methylcarbamoyl)pyridin-4-yloxy)phenylcarbamate
1129683-92-6

phenyl 4-(2-(methylcarbamoyl)pyridin-4-yloxy)phenylcarbamate

4-chloro-3-trifluoromethyl-aniline
320-51-4

4-chloro-3-trifluoromethyl-aniline

sorafenib
284461-73-0

sorafenib

Conditions
ConditionsYield
In acetonitrile for 24h; Product distribution / selectivity; Heating / reflux;
In acetonitrile for 24h; Reflux;
N-methyl-4-(4-(2,2,2-trichloroacetamido)phenoxy)picolinamide
1129683-94-8

N-methyl-4-(4-(2,2,2-trichloroacetamido)phenoxy)picolinamide

4-chloro-3-trifluoromethyl-aniline
320-51-4

4-chloro-3-trifluoromethyl-aniline

sorafenib
284461-73-0

sorafenib

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 110℃; for 8 - 9h; Product distribution / selectivity;
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 110℃;
C17H16ClF3N2O3

C17H16ClF3N2O3

sorafenib
284461-73-0

sorafenib

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogenchloride; water / 1 h / 40 °C / Inert atmosphere
2: t-BuBrettPhos; palladium diacetate; caesium carbonate / tetrahydrofuran; water / 5 h / 75 °C / Inert atmosphere
View Scheme
5-bromo-2-chlorobenzotrifluoride
445-01-2

5-bromo-2-chlorobenzotrifluoride

sorafenib
284461-73-0

sorafenib

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: t-BuBrettPhos; palladium diacetate; caesium carbonate / tetrahydrofuran; water / 2 h / 85 °C / Inert atmosphere
2: hydrogenchloride; water / 1 h / 40 °C / Inert atmosphere
3: t-BuBrettPhos; palladium diacetate; caesium carbonate / tetrahydrofuran; water / 5 h / 75 °C / Inert atmosphere
View Scheme
(1S)-10-camphorsulfonic acid
3144-16-9

(1S)-10-camphorsulfonic acid

sorafenib
284461-73-0

sorafenib

4-{4-[({[4-chloro-3-(trifluoromethyl)phenyl]amino}carbonyl)amino]phenoxy}-N-methylpyridine-2-carboxamide hemicamsylate

4-{4-[({[4-chloro-3-(trifluoromethyl)phenyl]amino}carbonyl)amino]phenoxy}-N-methylpyridine-2-carboxamide hemicamsylate

Conditions
ConditionsYield
In tert-butyl methyl ether at 15 - 50℃; Solvent; Temperature;99.4%
cis-dichlorobis(dimethylsulfoxide)platinum(II)
75992-73-3, 25794-47-2, 30729-25-0, 15274-33-6, 22840-91-1, 14568-13-9

cis-dichlorobis(dimethylsulfoxide)platinum(II)

sorafenib
284461-73-0

sorafenib

C23H22Cl3F3N4O4PtS

C23H22Cl3F3N4O4PtS

Conditions
ConditionsYield
In methanol; acetone at 45℃; for 28h; Solvent; Temperature;98%
2-aminobutanoic acid
2835-81-6

2-aminobutanoic acid

sorafenib
284461-73-0

sorafenib

sorafenib α-aminobutyrate

sorafenib α-aminobutyrate

Conditions
ConditionsYield
In water; isopropyl alcohol at 75℃; for 3h; Solvent; Temperature;97.9%
sorafenib
284461-73-0

sorafenib

4-[4-[[4-chloro-3-(trifluoromethyl)phenyl]carbamoylamino]phenoxy]-N-methyl-pyridine-2-carboxamide sulphate

4-[4-[[4-chloro-3-(trifluoromethyl)phenyl]carbamoylamino]phenoxy]-N-methyl-pyridine-2-carboxamide sulphate

Conditions
ConditionsYield
With sulfuric acid In butanone at 26℃; for 5h; Product distribution / selectivity;90.9%
sorafenib
284461-73-0

sorafenib

4-(4-{3-[4-chloro-3-(trifluoromethyl)phenyl]ureido}phenoxy)-N-methylpyridine-2-carboxamide sulphate
1280217-32-4

4-(4-{3-[4-chloro-3-(trifluoromethyl)phenyl]ureido}phenoxy)-N-methylpyridine-2-carboxamide sulphate

Conditions
ConditionsYield
With sulfuric acid In ethanol; water at 20 - 60℃; for 12h;89%
ethanesulfonic acid
594-45-6

ethanesulfonic acid

sorafenib
284461-73-0

sorafenib

4-[4-[[4-chloro-3-(trifluoromethyl)phenyl]carbamoylamino]phenoxy]-N-methyl-pyridine-2-carboxamide ethanesulphonate

4-[4-[[4-chloro-3-(trifluoromethyl)phenyl]carbamoylamino]phenoxy]-N-methyl-pyridine-2-carboxamide ethanesulphonate

Conditions
ConditionsYield
In butanone at 26℃; for 3h;88.9%
toluene-4-sulfonic acid
104-15-4

toluene-4-sulfonic acid

sorafenib
284461-73-0

sorafenib

N-[4-chloro-3-(trifluoromethyl)phenyl]-N′-[4-[2-(N-methylcarbamoyl)-4-pyridyloxy]phenyl]urea p-toluenesulfonate

N-[4-chloro-3-(trifluoromethyl)phenyl]-N′-[4-[2-(N-methylcarbamoyl)-4-pyridyloxy]phenyl]urea p-toluenesulfonate

Conditions
ConditionsYield
In water; acetonitrile Reflux;87.6%
In methanol at 40 - 65℃;84.5%
In acetonitrile at 26℃; for 2h;78.2%
sorafenib
284461-73-0

sorafenib

4-[4-[[4-chloro-3-(trifluoromethyl)phenyl]-carbamoylamino]phenoxy]-N-methyl-pyridine-2-carboxamide hydrochloride

4-[4-[[4-chloro-3-(trifluoromethyl)phenyl]-carbamoylamino]phenoxy]-N-methyl-pyridine-2-carboxamide hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In water; butanone at -10 - -5℃; for 3.16667h; Product distribution / selectivity;85.84%
methanesulfonic acid
75-75-2

methanesulfonic acid

sorafenib
284461-73-0

sorafenib

4-[4-[[4-chloro-3-(trifluoromethyl)phenyl]-carbamoylamino]phenoxy]-N-methyl-pyridine-2-carboxamide mesylate

4-[4-[[4-chloro-3-(trifluoromethyl)phenyl]-carbamoylamino]phenoxy]-N-methyl-pyridine-2-carboxamide mesylate

Conditions
ConditionsYield
In ethanol at 26 - 78℃; for 11h; Product distribution / selectivity;85.08%
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