819-46-5

Usage

Uses

Used in Pharmaceutical Industry:
4,4,4-Trifluorobutylamine is used as a key intermediate in the synthesis of various pharmaceuticals. Its unique properties allow it to contribute to the development of drugs with specific therapeutic effects, enhancing the range of treatments available for different medical conditions.
Used in Agrochemical Industry:
In the agrochemical sector, 4,4,4-Trifluorobutylamine serves as an essential component in the production of certain pesticides and other crop protection agents. Its incorporation can improve the effectiveness of these products, ensuring better agricultural yields and protection against pests.
Used in Fluorinated Compounds Synthesis:
4,4,4-Trifluorobutylamine is also utilized as a building block in the creation of other fluorinated compounds. The presence of fluorine atoms in these compounds can significantly alter their chemical and physical properties, making them suitable for a variety of specialized applications in different industries.

InChI:InChI=1/C4H8F3N/c5-4(6,7)2-1-3-8/h1-3,8H2

Upstream product

• 56-12-2 4-amino-n-butyric acid 
• 101055-03-2 4-azido-1,1,1-trifluorobutane 
• 461-34-7 4,4,4-trifluorobutyroamide 
• 107-10-8 propylamine 
• 887144-94-7 Togni's reagent II 
• 461-18-7 4,4,4-trifluorobutanol 

Downstream Products

• 1026837-41-1 3-Methoxy-4-[1-methyl-5-(4,4,4-trifluoro-butylcarbamoyl)-1H-indol-3-ylmethyl]-benzoic acid methyl ester 
• 84153-82-2 4,4,4-trifluorobutan-1-amine hydrochloride 
• 1589818-86-9 4-(2-methylthiazol-4-yl)-N-(4,4,4-trifluorobutyl)benzene sulfonamide 
• 1243325-58-7 3-nitro-4-(4,4,4-trifluorobutylamino)benzonitrile 

Relevant academic research and scientific papers

The merger of decatungstate and copper catalysis to enable aliphatic C(sp 3)–H trifluoromethylation

The introduction of a trifluoromethyl (CF3) group can dramatically improve a compound’s biological properties. Despite the well-established importance of trifluoromethylated compounds, general methods for the trifluoromethylation of alkyl C–H bonds remain elusive. Here we report the development of a dual-catalytic C(sp3)–H trifluoromethylation through the merger of light-driven, decatungstate-catalysed hydrogen atom transfer and copper catalysis. This metallaphotoredox methodology enables the direct conversion of both strong aliphatic and benzylic C–H bonds into the corresponding C(sp3)–CF3 products in a single step using a bench-stable, commercially available trifluoromethylation reagent. The reaction requires only a single equivalent of substrate and proceeds with excellent selectivity for positions distal to unprotected amines. To demonstrate the utility of this new methodology for late-stage functionalization, we have directly derivatized a broad range of approved drugs and natural products to generate valuable trifluoromethylated analogues. Preliminary mechanistic experiments reveal that a ‘Cu–CF3’ species is formed during this process and the critical C(sp3)–CF3 bond-forming step involves the copper catalyst. [Figure not available: see fulltext.].

NEW COMPOUNDS I/418

There is provided compounds of formula I, wherein R1 to R7 have meanings given in the description, which are useful in the prophylaxis and in the treatment of arrhythmias, in particular atrial and ventricular arrhythmias.

ANTIVIRAL 4-AMINOCARBONYLAMINO-SUBSTITUTED IMIDAZOLE COMPOUND

The invention relates to the substituted imidazoles of formula (I) and to methods for producing the same, to their use in the treatment and/or prophylaxis of diseases and to their use for producing drugs for use in the treatment and/or prophylaxis of diseases, especially for use as antiviral agents, especially against cytomegaloviruses.

Pyrimidine derivatives as IL-8 receptor antagonists

Compounds containing the pyrimidine nucleus and their use to treat diseases and conditions related to inappropriate Interleukin-8 receptor activity are disclosed. The compounds are of the formula I In these compounds, Q is preferably unsubstituted and substituted heterocyclyl; U is usually hydrogen or fluorine; and V is preferably hydrogen, halogen, alkyl, —O—alkyl or —S-alkyl. A representative example is:

IMIDAZOLYL PYRIMIDINE DERIVATIVES USEFUL AS IL-8 RECEPTOR MODULATORS

The invention relates to compounds of the formula I, wherein R1, R2, R3 and R4 are each independently selected from H, (1-4C)alkyl, (1-4C)alkoxy, trifluoromethyl, trifluoromethoxy, halogen, amino, sulfonamide, cyano, OH and nitro; R5 is H or (1-6C)alkyl;

Inhibitors of phenylethanolamine N-methyltransferase that are predicted to penetrate the blood-brain barrier: Design, synthesis, and evaluation of 3-fluoromethyl-7-(N-substituted aminosulfonyl)-1,2,3,4-tetrahydroisoquinolines that possess low affinity toward the α2-adrenoceptor

(±)-7-Aminosulfonyl-3-fluoromethyl-1,2,3,4-tetrahydroisoquinoline (7) is one of the most potent and selective inhibitors of phenylethanolamine N-methyltransferase (PNMT) reported to date, but a blood-brain barrier (BBB) model indicates that it cannot penetrate the BBB. To increase the lipophilicity of 7 by addition of a nonpolar substituent to the sulfonamide nitrogen, a small library of (±)-3-fluoromethyl-7-(N-substituted aminosulfonyl)-1,2,3,4- tetrahydroisoquinolines was synthesized and evaluated as inhibitors of PNMT and for affinity at the α2-adrenoceptor. In addition, this library probed the PNMT active site surrounding the sulfonamide nitrogen of 7. Bulky substituents on the sulfonamide nitrogen are disfavored at the PNMT active site more so than at the α2-adrenoceptor (thus reducing selectivity). On the other hand, alkyl chains on the sulfonamide nitrogen that contain an electron dense atom, such as a fluorine, are favored in the PNMT active site and possess little α2-adrenoceptor affinity, thereby conferring good selectivity (>500). Several members of the library (8, 14, 17, and 18) have excellent PNMT inhibitory potency and selectivity and are predicted, on the basis of their ClogP value (>0.5), to penetrate the BBB to a significant extent. Compounds 17 and 18 are the most potent and selective PNMT inhibitors reported to date.

Synthesis, Structure-Activity Relationships, and Pharmacological Evaluation of a Series of Fluorinated 3-Benzyl-5-indolecarboxamides: Identification of 4--1-methylindol-3-yl>methyl>-3-methoxy-N-benzamide, ...

The continued exploration of a series of 3-(arylmethyl)-1H-indole-5-carboxamides by the introduction of fluorinated amide substituents has resulted in the discovery of 4--1-methylindol-3-yl>methyl>-3-methoxy-N-benzamide (38p, ZENECA ZD 3523), which has been chosen for clinical evaluation.This compound exhibited a Ki of 0.42 nM for displacement of LTD4 on guinea pig lung membranes, a pKB of 10.13 +/- 0.14 versus LTE4 on guinea pig trachea, and an oral ED50 of 1.14 μmol/kg opposite LTD4-induced bronchoconstriction in guinea pigs.The R enantiomer was found to be modestly more potent than the S enantiomer 38o.Modification of the amide substituent to afford achiral compounds was unsuccessful in achieving comparable levels of activity.Profiling of 38p opposite a variety of functional assays has demonstrated the selectivity of this compound as a leukotriene receptor antagonist.The enantioselective synthesis of 38p, which employed a diastereoselective alkylation of (4R,5S)-3-(1-oxo-4,4,4-trifluorobutyl)-4-methyl-5-phenyl-2-oxazolidinone (27) as the key step to establish the chirality of the amide substituent, provided an efficient route for generating 38p in >99percent enantiomeric purity.

Deamination Reactions, 43 - The Effect of Trifluoromethyl Groups on the Reactivity of Aliphatic Diazonium Ions and Carbocations

Various trifluoroalkanamines (9, 26, 35, 38, 45, 56, and 67) have been prepared and diazotized (water, pH 3.5) to probe the effect of trifluoromethyl groups on the reactivity of aliphatic diazonium ions.The product distributions reveal that α-CF3 groups enhance inverting displacement and enforce rearrangement (hydride shifts) separating the positive charge from CF3.Migrations of the positive charge from the β- to the γ-position are less strongly promoted than those from α to β.Enhancement factors of ca. 15 (α -> β) and 4 (β -> γ) may be derived by comparison with analogous alkanediazonium ions.The positive charge does not migrate in the reverse direction (β -> α) except for minor amounts of a pinacolic rearrangement (68 -> 7).A migration of the positive charge from γ to β has been detected with 36 but a tenfold decrease as compared to the analogous butanediazonium ion 37 is indicated.All observations are reasonably explained in terms of the relative stabilities of the intermediate trifluoroalkyl cations.