365996-06-1

Basic information

• Product Name: tert-butyl 2-bromo-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H)-carboxylate
• Synonyms: tert-butyl 2-bromo-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H)-carboxylate;5-Boc-2-bromo-6,7-dihydro-4H-thiazolo[5,4-c]pyridine;tert-butyl 2-bromo-6,7-dihydro[1,3]thiazolo[5,4-c]pyridine-5(4H)-carboxylate;tert-butyl 2-broMo-6;2-BroMo-6,7-dihydro-4H-thiazolo[5,4-c]pyridine-5-carboxylicacidtert-butylester;2-Bromo-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine, N-BOC protected;Thiazolo[5,4-c]pyridine-5(4H)-carboxylic acid, 2-broMo-6,7-dihydro-, 1,1-diMethylethyl ester;tert-butyl 2-broMo-4H,5H,6H,7H-[1,3]thiazolo[5,4- c]pyridine-5-carboxylate
• CAS NO: 365996-06-1
• Molecular Formula: C₁₁H₁₅BrN₂O₂S
• Molecular Weight: 319.22
• Product Categories: CHIRAL CHEMICALS;Heterocycle-Pyridine series
• Mol File: 365996-06-1.mol

Chemical Properties

• Melting Point: 42-44 °C(Solv: ethyl ether (60-29-7))
• Boiling Point: 390.946 °C at 760 mmHg
• Flash Point: 190.238 °C
• Appearance: /
• Density: 1.496 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.58
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 1.23±0.20(Predicted)
• CAS DataBase Reference: tert-butyl 2-bromo-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H)-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl 2-bromo-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H)-carboxylate(365996-06-1)
• EPA Substance Registry System: tert-butyl 2-bromo-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H)-carboxylate(365996-06-1)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45
• RIDADR: UN2811
• Hazardous Substances Data: 365996-06-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Tert-butyl 2-bromo-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H)-carboxylate is used as a synthetic reagent for the production of tetrahydrothiazolopyridines. These compounds are known to be potent antagonists for the smoothened (Smo) receptor, which plays a crucial role in various cellular signaling pathways. By targeting the Smo receptor, tetrahydrothiazolopyridines can potentially be used in the development of therapeutic agents for conditions related to abnormal cellular signaling, such as certain types of cancer.
Additionally, the compound may also be utilized in the development of other pharmaceutical applications, given its unique chemical structure and reactivity. Further research and development in the pharmaceutical industry could lead to the discovery of new therapeutic agents and drug delivery systems that incorporate this compound.

InChI:InChI=1/C11H15BrN2O2S/c1-11(2,3)16-10(15)14-5-4-7-8(6-14)17-9(12)13-7/h4-6H2,1-3H3

Upstream product

• 7789-45-9 copper(II)bromide 
• 365996-05-0 tert-butyl 2-amino-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H)-carboxylate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 949922-52-5 2-bromo-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine hydrochloride 
• 540-80-7 tert.-butylnitrite 
• 188869-05-8 tert-butyl 3-bromo-4-oxo-piperidine-1-carboxylate 
• 79099-07-3 N-tert-butyloxycarbonylpiperidin-4-one 
• 207691-65-4 N-tert-butoxycarbonyl-4-(tetrahydropyrrole-1-yl)-1,2,3,6-tetrahydropyridine 

Downstream Products

• 165948-24-3 5-tert-Butoxycarbonyl-4,5,6,7-tetrahydrothiazolo[5,4-c]-pyridine 
• 165948-23-2 4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine 
• 1575609-63-0 (2R,3R)-3-(2-(2-methoxypyrimidin-5-yl)-6,7-dihydrothiazolo[5,4-c]pyridin-5(4H)-yl)-2-(2,4-di-fluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol 
• 1575609-62-9 (2R,3R)-3-(2-(2-methylpyrimidin-5-yl)-6,7-dihydrothiazolo[5,4-c]pyridin-5(4H)-yl)-2-(2,4-di-fluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol 
• 1575609-59-4 (2R,3R)-3-(2-(2-methoxypyridin-5-yl)-6,7-dihydrothiazolo[5,4-c]pyridin-5(4H)-yl)-2-(2,4-di-fluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol 
• 1575609-57-2 (2R,3R)-3-(2-(2-fluoropyridin-5-yl)-6,7-dihydrothiazolo[5,4-c]pyridin-5(4H)-yl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol 
• 1575609-55-0 (2R,3R)-2-(2,4-difluorophenyl)-3-(2-(pyrimidin-5-yl)-6,7-dihydrothiazolo[5,4-c]piperidine-5(4H)-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol 
• 1575609-52-7 (2R,3R)-2-(2,4-difluorophenyl)-3-(2-(2-cyanopyridin-5-yl)-6,7-dihydrothiazolo[5,4-c]piperidine-5(4H)-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol 
• 1575609-49-2 (2R,3R)-2-(2,4-difluorophenyl)-3-(2-(3-cyanopyridin-5-yl)-6,7-dihydrothiazolo[5,4-c]piperidine-5(4H)-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol 
• 1575609-48-1 (2R,3R)-2-(2,4-difluorophenyl)-3-(2-(3-fluoropyridin-5-yl)-6,7-dihydrothiazolo[5,4-c]piperidine-5(4H)-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol 
• 1575609-46-9 (2R,3R)-2-(2,4-difluorophenyl)-3-(2-(pyridin-3-yl)-6,7-dihydrothiazolo[5,4-c]piperidine-5(4H)-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol 
• 1575609-43-6 (2R,3R)-2-(2,4-difluorophenyl)-3-(2-(pyridin-4-yl)-6,7-dihydrothiazolo[5,4-c]piperidine-5(4H)-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol 
• 1575609-41-4 (2R,3R)-3-(2-(thiophen-3-yl)-6,7-dihydrothiazolo[5,4-c]pyridin-5(4H)-yl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol 
• 1575609-38-9 (2R,3R)-3-(2-(furan-2-yl)-6,7-dihydrothiazolo[5,4-c]pyridin-5(4H)-yl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol 

Relevant articles and documents

1-[2-(1-Cyclobutylpiperidin-4-yloxy)-6,7-dihydro-4H-thiazolo[5,4-c]pyridin-5-yl]propan-1-one: a Histamine H3 Receptor Inverse Agonist with Efficacy in Animal Models of Cognition

A series of chemical optimizations, which was guided by in vitro affinity at histamine H3 receptor (H3R), modulation of lipophilicity, ADME properties and preclinical efficacy resulted in the identification of 1-[2-(1-cyclobutylpiperidin-4-yloxy)-6,7-dihydro-4H-thiazolo[5,4-c]pyridin-5-yl]propan-1-one (45 e) as a potent and selective (Ki=4.0 nM) H3R inverse agonist. Dipsogenia induced by (R)-α-methylhistamine was dose dependently antagonized by 45 e, confirming its functional antagonism at H3R. It is devoid of hERG and phospholipidosis issues. Compound 45 e has adequate oral exposures and favorable half-life in both rats and dogs. It has demonstrated high receptor occupancy (ED80=0.22 mg/kg) and robust efficacy in object recognition task and, dose dependently increased acetylcholine levels in brain. The sub-therapeutic doses of 45 e in combination with donepezil significantly increased acetylcholine levels. The potent affinity, selectivity, in vivo efficacy and drug like properties together with safety, warrant for further development of this molecule for potential treatment of cognitive disorders associated with Alzheimer's disease.

NOVEL MORPHOLINYL AMINE COMPOUNDS FOR THE TREATMENT OF AUTOIMMUNE DISEASE

The present invention relates to compounds of formula (I), wherein R1, R2 and R3 are as described herein, and their pharmaceutically acceptable salt, enantiomer or diastereomer thereof, and compositions including the compounds and methods of using the compounds.

BICYCLIC HETEROARYL SUBSTITUTED COMPOUNDS

Disclosed are compounds of Formula (I) to (VIII): (I) (II) (III) (IV) (V) (VI) (VII) (VIII); or a stereoisomer, tautomer, pharmaceutically acceptable salt, solvate or prodrug thereof, wherein R3 is a bicyclic heteroaryl group substituted with zero to 3 R3a; and R1, R2, R3a, R4, and n are defined herein. Also disclosed are methods of using such compounds as PAR4 inhibitors, and pharmaceutical compositions comprising such compounds. These compounds are useful in inhibiting or preventing platelet aggregation, and are useful for the treatment of a thromboembolic disorder or the primary prophylaxis of a thromboembolic disorder.

Substituted tetrahydroisoquinoline compound and application

The invention discloses a substituted tetrahydroisoquinoline compound and application. The compound has a structure as shown in a general formula I in the specification; and in the general formula I, substituents are defined in the specification. The comp

Substituted amide compound and application

The invention belongs to the field of agricultural bactericidal, insecticidal and acaricidal agents, and relates to a substituted amide compound and an application. The substituted amide compound has a structure as shown in a general formula I in the specification; and in the general formula I, substituents are defined in the specification. The compound provided by the invention has broad-spectrum bactericidal, insecticidal and acaricidal activities, has excellent control effects on diseases like cucumber downy mildew, corn rust, wheat powdery mildew and rice blast, especially has better control effects on the corn rust, also has excellent control effects on aphids and Tetranychus cinnabarinus, and especially can obtain good effects on the Tetranychus cinnabarinus at a low dosage.

PRMT5 INHIBITORS AND USES THEREOF

Described herein are compounds of Formula (A), pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof:wherein Y1 is of formula (?) or formula (y):Ring Y is a 5- to 6-membered heteroaryl ring; and V4, V5, Rx, x, y, and n are as defined herein. Compounds of the present invention are useful for inhibiting PRMT5 activity. Methods of using the compounds for treating PRMT5-mediated disorders are also described.

ANTI-INFECTIVE COMPOUNDS

The present invention relates to small molecule compounds having the general formula (I): wherein A is a moiety selected from the group consisting of formulae (A) to (K) and their use in the treatment of bacterial infections, in particular Tuberculosis.

Design, synthesis, and structure-activity relationship studies of novel fused heterocycles-linked triazoles with good activity and water solubility

Triazoles with fused-heterocycle nuclei were designed and evaluated for their in vitro activity on the basis of the binding mode of albaconazole using molecular docking, along with SAR of antifungal triazoles. Tetrahydro-[1,2,4] triazolo[1,5-a]pyrazine and tetrahydro-thiazolo[5,4-c]pyridine nuclei were preferable to the other four fused-heterocycle nuclei investigated. Potent in vitro activity, broad spectrum and better water solubility were attained when triazoles containing nitrogen aromatic heterocycles were attached to these two nuclei. The most potent compounds 27aa and 45x, with low hERG inhibition and hepatocyte toxicity, both exhibited excellent activity against Candida, Cryptococcus, and Aspergillus spp., as well as selected fluconazole-resistant strains. A high water-soluble compound 58 (the disulfate salt of 45x) displayed unsatisfactory in vivo activity because of its poor PK profiles. Mice infected with C.alb. SC5314 and C.alb. 103 (fluconazole-resistant strain) and administered with 27aa displayed significantly improved survival rates. 27aa also showed favorable pharmacokinetic (PK) profiles.

HEDGEHOG PATHWAY SIGNALING INHIBITORS AND THERAPEUTIC APPLICATIONS THEREOF

The hedgehog (Hh) signaling pathway is a pathway which regulates patterning, growth and cell migration during embryonic development, but in adulthood is limited to tissue maintenance and repair. Mutational inactivation of the inhibitory pathway components leads to constitutive ligand-independent activation of the Hh signaling pathway, results in cancers such as basal cell carcinoma and medulloblastoma. Ligand-dependent activation of Hh signaling is involved in prostate cancer, pancreatic cancer, breast cancer and blood cancers. Therefore, inhibition of the aberrant Hh signaling represents a promising approach toward novel anticancer therapy. The invention provides novel molecules of formula I that inhibit hedgehog pathway signaling and provides therapeutic applications for the treatment of malignancies (basal cell carcinoma, medulloblastoma, glioblastoma, non-small cell lung cancer, prostate cancer, pancreatic cancer, blood cancers, mesenchymal cancers, etc.), prevention of tumor regrowth, sensitization of radio-chemo therapies, and other diseases (inflammation, fibrosis and immune disorders).

PROCESS FOR PREPARING A COMPOUND BY A NOVEL SANDMEYER-LIKE REACTION USING A NITROXIDE RADICAL COMPOUND AS A REACTION CATALYST

The present invention provides a novel process for preparing a substituted aromatic compound such as an aromatic halo compound or a salt thereof through a transformation reaction of an aromatic diazonium salt from an aromatic amino compound at stable high yields utilizing a novel Sandmeyer-like reaction using a nitroxide radical compound as a reaction catalyst.