[ CAS No. 874-38-4 ] {[proInfo.proName]}

Name: 874-38-4|6-Methylimidazo[1,2-a]pyridine|98%
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SKU: A596162
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Quality Control of [ 874-38-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 874-38-4 ]

SDS Specification

Alternatived Products of [ 874-38-4 ]

Product Details of [ 874-38-4 ]

CAS No. :	874-38-4	MDL No. :	MFCD05663806
Formula :	C₈H₈N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VKVFDPQDGZSLJK-UHFFFAOYSA-N
M.W :	132.16	Pubchem ID :	2764325
Synonyms :

Calculated chemistry of [ 874-38-4 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.12
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	40.16
TPSA :	17.3 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) :	-5.59 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.93
Log Po/w (XLOGP3) :	2.13
Log Po/w (WLOGP) :	1.64
Log Po/w (MLOGP) :	1.05
Log Po/w (SILICOS-IT) :	1.45
Consensus Log Po/w :	1.64

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.67
Solubility :	0.284 mg/ml ; 0.00215 mol/l
Class :	Soluble
Log S (Ali) :	-2.12
Solubility :	0.992 mg/ml ; 0.0075 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.44
Solubility :	0.483 mg/ml ; 0.00366 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.36

Safety of [ 874-38-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H320-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 874-38-4 ]

* 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.

Downstream synthetic route of [ 874-38-4 ]

[ 874-38-4 ] Synthesis Path-Downstream 1~55

1
[ 1603-41-4 ]
[ 107-20-0 ]
[ 874-38-4 ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 4415 - 4424
[2]Journal of Medicinal Chemistry,2021,vol. 64,p. 1197 - 1219

2
[ 137415-94-2 ]
[ 874-38-4 ]
6-Methyl-1-(5-oxo-4,4-diphenyl-tetrahydro-furan-2-ylmethyl)-1H-imidazo[1,2-a]pyridin-4-ylium; chloride [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 4415 - 4424

3
[ 874-38-4 ]
[ 74-88-4 ]
[ 15639-32-4 ]

Reference： [1]Tetrahedron,1981,vol. 37,p. 91 - 95

4
[ 874-38-4 ]
[ 144042-80-8 ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 4415 - 4424

5
[ 50-00-0 ]
[ 874-38-4 ]
[ 217435-67-1 ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 5108 - 5112

7
[ 874-38-4 ]
3-benzylsulfanylmethyl-6-methyl-imidazo[1,2-<i>a</i>]pyridine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 5108 - 5112

8
3-(3-Oxobutyryloxymethyl)-7β-[2-(2-tritylaminothiazol-4-yl)-2(Z)-(1-methyl-1tert-butoxycarbonylethoxyimino)acetamido]-3-cephem-4-carboxylic acid [ No CAS ]
[ 874-38-4 ]
7β-[2-(2-Aminothiazol-4-yl)-2(Z)-(1-carboxy-1-methylethoxyimino)acetamido]-3-[(6-methylimidazo[1,2-a]pyridinium-1-yl)methyl]-3-cephem-4-carboxylate monosodium salt [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		3-(3-Oxobutyryloxymethyl)-7β-[2-(2-tritylaminothiazol-4-yl)-2(Z)-(1-methyl-1-tert-butoxycarbonylethoxyimino)acetamido]-3-cephem-4-carboxylic acid is reacted with <strong>[874-38-4]6-methylimidazo[1,2-a]pyridine</strong> in the same manner as described in Example 5 to give the above-identified compound. Elemental analysis for: C25 H24 N7 O7 S2 Na.4H2 O: Calcd. (%): C, 43.29; H, 4.65; N, 14.13. Found (%): C, 43.76, H, 4.55; N, 13.59. IR spectrum νmaxKBr cm-1: 1770, 1660, 1600, 1525. NMR spectrum (d6 -DMSO) δ: 1.43 (6H, s), 2.43 (3H, s), 4.99 (1H, d, J=4.5 Hz), 5.33 (2H, br. s), 5.66 (1H, d. d, J=4.5 Hz & 8 Hz), 6.70 (1H, s), 7.13 (2H, br. s), 7.68-8.02 (1H, m), 8.06-8.6 (3H, m), 8.64-8.88 (1H, m), 11.54 (1H, d, J=8 Hz).

Reference： [1]Patent: US4788185,1988,A

9
[ 1073-06-9 ]
[ 874-38-4 ]
[ 1467064-06-7 ]

Reference： [1]Bulletin of the Korean Chemical Society,2013,vol. 34,p. 2340 - 2342

10
[ 874-38-4 ]
[ 108-67-8 ]
[ 1560900-29-9 ]

Yield	Reaction Conditions	Operation in experiment
29%	With oxygen; palladium diacetate; silver carbonate; Trimethylacetic acid; In N,N-dimethyl-formamide; at 130℃; for 20h;	General procedure: imidazo[1,2-a]pyridine 1a (118mg, 1 mmol), benzene ( 2a, 1 mL), Pd(OAc)2 (5 mol%), Ag2CO3(5 mol%) and PivOH (1.2 eq) were stirred in DMF (2 mL) at 130 C equipped with oxygen bag for 20 h. After completion of the reaction (monitored by TLC),the water (10mL) was added. The aqueous solution was extracted with ethyl acetate (3×15 mL) and the combined extract was dried with anhydrous MgSO4.The solvent was removed and the crude product was separated by column chromatography (eluted with petroleum ether : ethyl acetate=21) to give a pure sample of 3a (Yellowoil, 144 mg, yield 74%).

Reference： [1]Tetrahedron Letters,2014,vol. 55,p. 1589 - 1592

11
[ 95-47-6 ]
[ 874-38-4 ]
[ 1560900-37-9 ]

Yield	Reaction Conditions	Operation in experiment
75%	With oxygen; palladium diacetate; silver carbonate; Trimethylacetic acid; In N,N-dimethyl-formamide; at 130℃; for 20h;	General procedure: imidazo[1,2-a]pyridine 1a (118mg, 1 mmol), benzene ( 2a, 1 mL), Pd(OAc)2 (5 mol%), Ag2CO3 (5 mol%) and PivOH (1.2 eq) were stirred in DMF (2 mL) at 130 C equipped with oxygen bag for 20 h. After completion of the reaction (monitored by TLC),the water (10mL) was added. The aqueous solution was extracted with ethyl acetate (3×15 mL) and the combined extract was dried with anhydrous MgSO4.The solvent was removed and the crude product was separated by column chromatography (eluted with petroleum ether : ethyl acetate=21) to give a pure sample of 3a (Yellowoil, 144 mg, yield 74%).

Reference： [1]Tetrahedron Letters,2014,vol. 55,p. 1589 - 1592

12
[ 292638-85-8 ]
[ 874-38-4 ]
[ 1642164-63-3 ]

Reference： [1]RSC Advances,2014,vol. 4,p. 32013 - 32016

13
[ 141-32-2 ]
[ 874-38-4 ]
[ 1642164-61-1 ]

Reference： [1]RSC Advances,2014,vol. 4,p. 32013 - 32016

14
[ 107-13-1 ]
[ 874-38-4 ]
C₁₁H₉N₃ [ No CAS ]

Reference： [1]RSC Advances,2014,vol. 4,p. 32013 - 32016

15
[ 5720-05-8 ]
[ 874-38-4 ]
6-methyl-3-(p-tolyl)imidazo[1,2-a]pyridine [ No CAS ]

Reference： [1]Catalysis Communications,2014,vol. 56,p. 65 - 67

16
[ 768-35-4 ]
[ 874-38-4 ]
[ 1467064-06-7 ]

Reference： [1]Catalysis Communications,2014,vol. 56,p. 65 - 67

17
[ 100-42-5 ]
[ 874-38-4 ]
C₁₆H₁₄N₂ [ No CAS ]

Reference： [1]RSC Advances,2014,vol. 4,p. 50137 - 50140

18
[ 405-99-2 ]
[ 874-38-4 ]
C₁₆H₁₃FN₂ [ No CAS ]

Reference： [1]RSC Advances,2014,vol. 4,p. 50137 - 50140

19
[ 141-32-2 ]
[ 874-38-4 ]
C₁₅H₁₈N₂O₂ [ No CAS ]

Reference： [1]RSC Advances,2014,vol. 4,p. 50137 - 50140

20
[ 292638-85-8 ]
[ 874-38-4 ]
C₁₂H₁₂N₂O₂ [ No CAS ]

Reference： [1]RSC Advances,2014,vol. 4,p. 50137 - 50140

21
[ 67-68-5 ]
[ 874-38-4 ]
6-methylimidazo[1,2-a]pyridine-3-carbaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With iron(III) chloride; oxygen; acetic acid; at 100℃; under 760.051 Torr; for 12h;	General procedure: FeCl3 (0.025 mmol, 4 mg) and AcOH (0.1 mmol, 6 mg) was mixed with DMSO (3 mL) in a glass vial or round-bottom flask equipped with a magnetic stirring bar. Then, substrate 1 (0.5 mmol) was added. The mixture was stirred under an dioxygen atmosphere (1 atm) at 100C for 12 h. After cooling down to room temperature, 5 mL of ethyl acetate was added and removal of the DMSO with brine, the residue was purified by flash chromatography on silica gel to obtain the desired product 2 using light petroleum ether/ethyl acetate (4:1, v/v) as eluent, which furnished the 3-formylimidazo[1,2-a]pyridine.

Reference： [1]Chemical Communications,2015,vol. 51,p. 1823 - 1825
[2]Tetrahedron Letters,2016,vol. 57,p. 3870 - 3872

22
[ 2206-27-1 ]
[ 874-38-4 ]
C₉H₇⁽²⁾HN₂O [ No CAS ]

Reference： [1]Chemical Communications,2015,vol. 51,p. 1823 - 1825

23
[ 149-30-4 ]
[ 874-38-4 ]
C₁₅H₁₁N₃S₂ [ No CAS ]

Reference： [1]Catalysis Communications,2015,vol. 66,p. 83 - 86

24
[ 874-38-4 ]
[ 60-56-0 ]
C₁₂H₁₂N₄S [ No CAS ]

Reference： [1]Catalysis Communications,2015,vol. 66,p. 83 - 86

25
[ 371-42-6 ]
[ 874-38-4 ]
3-((4-fluorophenyl)thio)-6-methylimidazo[1,2-a]pyridine [ No CAS ]

Reference： [1]Catalysis Communications,2015,vol. 66,p. 83 - 86

26
[ 7217-59-6 ]
[ 874-38-4 ]
C₁₅H₁₄N₂OS [ No CAS ]

Reference： [1]Catalysis Communications,2015,vol. 66,p. 83 - 86

27
[ 874-38-4 ]
[ 1972-28-7 ]
diethyl 1-(6-methylimidazo[1,2-a]pyridin-3-yl)hydrazine-1,2-dicarboxylate [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2015,vol. 13,p. 2958 - 2964

28
[ 75-33-2 ]
[ 874-38-4 ]
C₁₁H₁₄N₂S [ No CAS ]