[ CAS No. 109-04-6 ] {[proInfo.proName]}

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Quality Control of [ 109-04-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 109-04-6 ]

Product Citations Expand+

Systematic Study of Heteroarene Stacking Using a Congeneric Set of Molecular Glues for Procaspase-6

Togo, Takaya ; Tram, Linh ; Denton, Laura G. , et al. J. Med. Chem.,2023,66(14):9784-9796. DOI: 10.1021/acs.jmedchem.3c00590 PubMed ID: 37406165

Abstract: Heteroaromatic stacking interactions are important in drug binding, supramolecular chemistry, and materials science, making protein-ligand model systems of these interactions of considerable interest. Here we studied 30 congeneric ligands that each present a distinct heteroarene for stacking between tyrosine residues at the dimer interface of procaspase-6. Complex X-ray crystal structures of 10 analogs showed that stacking geometries were well conserved, while high-accuracy computations showed that heteroarene stacking energy was well correlated with predicted overall ligand binding energies. Empirically determined KD values in this system thus provide a useful measure of heteroarene stacking with tyrosine. Stacking energies are discussed in the context of torsional strain, the number and positioning of heteroatoms, tautomeric state, and coaxial orientation of heteroarene in the stack. Overall, this study provides an extensive data set of empirical and high-level computed binding energies in a versatile new protein-ligand system amenable to studies of other intermolecular interactions.

Purchased from AmBeed: 56423-63-3 ; 88491-61-6 ; 72287-26-4 ; 109-04-6

Synthesis of MAPA reagents and 2-alkyl (aryl) aminopyridines from 2-bromopyridine using the goldberg reaction

Comins, Daniel L ; Molecules,2022,27(6):1833. DOI: 10.3390/molecules27061833 PubMed ID: 35335206

Abstract: A short and economical synthesis of various 2-methylaminopyidine amides (MAPA) from 2-bromopyridine has been developed using the catalytic Goldberg reaction. The effective catalyst was formed in situ by the reaction of CuI and 1,10-phenanthroline in a 1/1 ratio with a final loading of 0.5–3 mol%. The process affords high yields and can accommodate multigram-scale reactions. A modification of this method provides a new preparation of 2-N-substituted aminopyridines from various secondary N-alkyl(aryl)formamides and 2-bromopyridine. The intermediate aminopyridine formamide is cleaved in situ through methanolysis or hydrolysis to give 2-alkyl(aryl)aminopyridines in high yields.

Keywords: N-methyl-N-(2-pyridyl)formamide ; 2-methylaminopyridine amides ; 2-alkyl(aryl)aminopyridines ; Goldberg reaction ; copper-catalyzed reactions ; cross-coupling reactions ; 1,10-phenanthroline

Purchased from AmBeed: 123-39-7 ; 109-04-6

Product Details of [ 109-04-6 ]

CAS No. :	109-04-6	MDL No. :	MFCD00006219
Formula :	C₅H₄BrN	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	IMRWILPUOVGIMU-UHFFFAOYSA-N
M.W :	158.00	Pubchem ID :	7973
Synonyms :

Calculated chemistry of [ 109-04-6 ] Expand+

Physicochemical Properties

Num. heavy atoms :	7
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	31.94
TPSA :	12.89 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.26 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.62
Log Po/w (XLOGP3) :	1.42
Log Po/w (WLOGP) :	1.84
Log Po/w (MLOGP) :	1.24
Log Po/w (SILICOS-IT) :	2.18
Consensus Log Po/w :	1.66

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.35
Solubility :	0.708 mg/ml ; 0.00448 mol/l
Class :	Soluble
Log S (Ali) :	-1.3
Solubility :	8.0 mg/ml ; 0.0506 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.86
Solubility :	0.217 mg/ml ; 0.00137 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.61

Safety of [ 109-04-6 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:
Hazard Statements:	H302-H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 109-04-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 109-04-6 ]
Downstream synthetic route of [ 109-04-6 ]

[ 109-04-6 ] Synthesis Path-Upstream 1~1

1
[ 109-04-6 ]
[ 927-74-2 ]
[ 395652-44-5 ]

Yield	Reaction Conditions	Operation in experiment
90%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In 1,4-dioxane at 20℃; Inert atmosphere	Under nitrogen atmosphere, and at r.t., CuT (0.06 g, 0.31 mmol), dry Et3N (1.32 mL, 9.49 mmol) and bis-(triphenylphosphine)-palladium chloride (0.13 g, 0.18 mmol) were sequentially added to a solution of 2-bromopyridine (0.60 mL, 6.33 mmol) in 1,4-dioxane (10 mL). Then, but-3-yn-1-ol (0.57 mL, 7.59 mmol) was added dropwise at the same temperature.The resulting reaction mixture was left stirred overnight, then concentrated under reduced pressure, dissolved in EtOAc (80 mL) and washed with H20 (3 x 10 mL). The organic layer was dried over Na2504 and concentrated to dryness to give an oily crude (1.1 g). Purification by typical silica gel flash chromatography using a Teledyne ISCO apparatus (Cy/EtOAc from 90:10 to 30:70) afforded the pure title compound (0.84 g, 90percent), as a white solid. R= 1.25 mm. MS(ESI) m/z: 148 EM-H], 170 EM-Na], 186 EM-K]. ‘H NMR (DMSO-d6): ö 8.55—8.49 (m, 1H),7.76 (td, 1H, J= 7.8, 1.8 Hz), 7.44 (d, 1H, J= 7.8 Hz), 7.33 (ddd, 1H, J= 7.8, 4.9, 1.8 Hz), 4.92 (t, 1H, J= 5.2 Hz), 3.62-3.58 (m, 2H), 2.58 (t, 2H, J= 6.8 Hz).
77%	at 0 - 70℃;	Example 199 ;3 -Methoxy- N -methyl- N -( 4-(pyridin- 2-yl)but - 3 -ynyl)benzamide; 199(A) 4-(Pyridin-2-yl)but-3-yn-1-01; To a suspension of CuI (301 mg, 1.58 mmol) in TEA (40 mL) were added 2- bromopyridine (5 g, 31.6 mmol), followed by Pd2Cl2(PPh3)2 (1.11 g, 1.58 mmol) to give a yellow orange suspension. After cooling down to 0°C under N2, 3-butyn-l-ol (2.28 g, 31.6 mmol) was added. The resulting reaction mixture turned black and it was stirred overnight at 70°C. The reaction mixture was quenched at 0°C with water, TEA was removed under low pressure, and the organic layer was extracted 3x using DCM, washed with Ammonia, water, brine, dried over MgS04, filtered and concentrated. The crude residue was purified over silicagel chromatography (prepacked 250 g silicagel column, DCM/MeOH : from 99/1 to 95/5 as eluent) to afford 3.60 g of 4- (pyridin-2-yl)but-3-yn-1-ol as a brown oil (Yield : 77percent). LCMS (RT) : 1.58min; MS (ES+) gave m/z : 148 Rf (DCM/MeOH : 95/5) =0.23

Reference： [1] Tetrahedron Letters, 2005, vol. 46, # 10, p. 1717 - 1720
[2] Journal of Organic Chemistry, 2003, vol. 68, # 3, p. 762 - 769
[3] Patent: WO2014/144836, 2014, A2, . Location in patent: Paragraph 0526; 0527
[4] European Journal of Organic Chemistry, 2011, # 2, p. 271 - 279
[5] Patent: WO2005/123703, 2005, A2, . Location in patent: Page/Page column 207
[6] Molecules, 2010, vol. 15, # 12, p. 9157 - 9173
[7] Journal of Organic Chemistry, 2003, vol. 68, # 8, p. 3327 - 3329
[8] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 8, p. 1077 - 1080

Yield	Reaction Conditions	Operation in experiment
60%	With potassium tert-butylate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl;tris-(dibenzylideneacetone)dipalladium(0); In toluene; at 90℃; for 17h;Inert atmosphere;	2-Amino-isoquinoline (301 mg, 2.09 mmol), 2-bromopyridine (181muL, 1.90 mmol), tBuOK (320 mg, 2.55 mmol), (+/-)-BINAP (47 mg, 0.08 mmol) and Pd2(dba)3 (43 mg, 0.05 mmol) were stirred in toluene (3 mL) at 9O0C under Ar(g) for 17h. The reaction mixture was then diluted with CH2CI2 (5mL) and silica was added followed by the removal of the solvent under reduced pressure. The resulting dry loaded material was purified by silica gel column chromatography eluting with hexane/EtOAc (80:20 then 70:30) to furnish I as a white solid (252 mg, 60percent).1H NMR (400MHz, CDCI3) deltaH: 8.99 (s, 1H), 8.34 (d, J=4.0Hz, 1H), 8.28 (s, 1H), 7.87 (d, J=8.5Hz, 1 H), 7.78 (d, J=8.5Hz, 1 H), 7.67-7.55 (m, 2H), 7.39 (t, J=7.5Hz, 1H), 7.19 (d, J=7.5Hz, 1H), 6.91-6.84 (m, 1H). MW: 221.26. LCMS (ES): found 222.1 [MH]+.

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Technical Information

• Alkyl Halide Occurrence • General Reactivity • Grignard Reaction • Hiyama Cross-Coupling Reaction • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Preparation of Amines • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Dihalides • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling

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Related Parent Nucleus of
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