[ CAS No. 182181-42-6 ]

Name: 182181-42-6|2-(Chloromethyl)-8-methylimidazo[1,2-a]pyridine|95%
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Quality Control of [ 182181-42-6 ]

COA NMR CNMR HPLC LC-MS

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SDS

Alternatived Products of [ 182181-42-6 ]

Product Details of [ 182181-42-6 ]

CAS No. :	182181-42-6	MDL No. :	MFCD00269518
Formula :	C₉H₉ClN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	180.63 g/mol	Pubchem ID :	3254999
Synonyms :

Calculated chemistry of of [ 182181-42-6 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.22
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	49.92
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) :	2.21
Log Po/w (XLOGP3) :	2.55
Log Po/w (WLOGP) :	2.23
Log Po/w (MLOGP) :	1.67
Log Po/w (SILICOS-IT) :	2.33
Consensus Log Po/w :	2.2

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.06
Solubility :	0.159 mg/ml ; 0.00088 mol/l
Class :	Soluble
Log S (Ali) :	-2.56
Solubility :	0.497 mg/ml ; 0.00275 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.49
Solubility :	0.0582 mg/ml ; 0.000322 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.85

Safety of [ 182181-42-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 182181-42-6 ]

* 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 [ 182181-42-6 ]
Downstream synthetic route of [ 182181-42-6 ]

[ 182181-42-6 ] Synthesis Path-Upstream 1~1

1
[ 1603-40-3 ]
[ 534-07-6 ]
[ 182181-42-6 ]

Reference： [1] Patent: WO2005/68432, 2005, A1, . Location in patent: Page/Page column 201

[ 182181-42-6 ] Synthesis Path-Downstream 1~5

1
[ 474889-56-0 ]
[ 182181-42-6 ]
[ 861135-05-9 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In DMF (N,N-dimethyl-formamide); at 0 - 20℃; for 7h;	Production Example 28; 1.52 g of 2- (chloromethyl)-8-methylimidazo [1, 2- pyridine and 1.36 g of (3,3, 3- trifluoropropyl) malononitrile were dissolved in 20 ml of N, N-dimethylformamide, and 1.16 g of potassium carbonate was then added under ice-cooling. The mixture was stirred at room temperature for 7 hours. After water was added, the reaction mixture was extracted with methyl-t-butyl ether. The organic layer was washed with water, dried over anhydrous magnesium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and then recrystallized form hexane-ethyl acetate to obtain 1.50 g of a compound represented by the following formula: (hereinafter, referred to as the present compound (28)). 1H-NMR (CDCl3, TMS, 8 (ppm) ): 2. 38-2. 42 (2H, m), 2.54-2. 66 (2H, m), 2.57 (3H, s), 3.53 (2H, s), 6.73 (1H, t), 7.00 (1H, dd), 7.66 (1H, s), 7.97 (1H, d)

Reference： [1]Patent: WO2005/68432,2005,A1 .Location in patent: Page/Page column 142-143

2
[ 1603-40-3 ]
[ 534-07-6 ]
[ 182181-42-6 ]

Yield	Reaction Conditions	Operation in experiment
		Reference Production Example 23; 2-(Chlromethyl)-8-methylimidazo [1, 2-a] pyridine; 3. 81 g of 1,3-dichloroacetone and 3.24 g of 2-amino-3- methylpyridine were dissolved in 30 ml of ethanol, and the solution was heated to reflux for 5 hours. The reaction mixture was cooled to room temperature and then concentrated under reduced pressure. To the residue, 50 ml of aqueous saturated sodium hydrogen carbonate was added and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and then recrystallized from hexane-methyl-t-butyl ether to obtain 1.52 g of 2-(chloromethyl)-8-methylimidazo [1, 2-a] pyridine. H-NMR (CDCl3, TMS, 8 (ppm) ): 2.60 (3H, s), 4.80 (2H, s), 6.68 (1H, t), 6.96 (1H, dd), 7.61 (1H, s), 7.93 (1H, d)

Reference： [1]Patent: WO2005/68432,2005,A1 .Location in patent: Page/Page column 201

Yield	Reaction Conditions	Operation in experiment
		Step 1. 2-(Chloromethyl)-8-methylimidazo[1,2-a]pyridine A mixture of 2-amino-3-picoline (Aldrich; 13.23 g), 1,3-dichloroacetone (Aldrich; 18.92 g), and dimethoxyethane (131 mL) is stirred at room temperature for 2 days. The mixture is then concentrated under reduced pressure and ethanol (100 mL) is added. The mixture is heated at 80 C. for 2.3 h. After cooling, the mixture is concentrated under reduced pressure and the residue is partitioned between saturated aq. sodium bicarbonate and dichloromethane. The combined organic layers are dried with MgSO4 and concentrated under reduced pressure. The residue is chromatographed on silica gel first using methanol/dichloromethane (4/96) and a second time using methanol/dichloromethane (2/98). The appropriate fractions are combined and concentrated, and the residue is crystallized from ethyl acetate/dichloromethane/ether to give a first crop of 5.854 g and a second crop of 1.079 g of 2-(chloromethyl)-8-methylimidazo[1,2-a]pyridine; MS m/z 180, 182; IR (mineral oil) 752, 709, 1259, 773, 1493 cm-1; 1 H NMR (CDCl3) delta2.61, 4.80, 6.70, 6.97, 7.62, 7.95.

4
[ 182181-42-6 ]
[ 872362-99-7 ]

Yield	Reaction Conditions	Operation in experiment
100%		67(D) 8-Methyi-2-(4-(trimethyisiiyi)but-3-ynyl)-imidazo[1,2-a]pvridine ;To a solution of trimethyl(prop-1-ynyl)silane (259 mg, 2.31 mmol) in THF (7.5 mL) at -78C was added n-BuLi 2.5M in hexane (1.1 mL, 2.8 mmol). After 90min at -78C <strong>[182181-42-6]2-(chloromethyl)-8-methyl-imidazo[1,2-a]pyridine</strong> (500 mg, 2.8 mmol) in THF (5 mL) was added dropwise. The solution became blue-green at-78C. The solution was stirred at-78C for an additional 1h. The reaction was quenched with water and the solvent was removed under reduced pressure. The crude product was purified over silicagel chromatography (prepacked 25 g silicagel column, DCM/MeOH from 100/0 to 99/1 as eluent) to afford 590 mg of 8-methyl-2-(4-(trimethylsilyl)but-3-ynyl)- imidazo[1,2-a]pyridine (Yield : 100%) as an yellow oil. LCMS (RT) : 0.59-2.61min; MS (ES+) gave m/z : 257.1 Rf (DCM/MeOH : 95/5) : 0.22

Reference： [1]Patent: WO2005/123703,2005,A2 .Location in patent: Page/Page column 125

5
[ 182181-42-6 ]
[ 1013-78-1 ]
2-[[4-(2,4-dichlorophenyl)-1-piperazinyl]methyl]-8-methylimidazo[1,2-a]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane;	EXAMPLE 55 2-[[4-(2,4-Dichlorophenyl)-1-piperazinyl]methyl]-8-methylimidazo[1,2-a]pyridine monomaleic acid salt. Refer to Chart E A mixture of <strong>[182181-42-6]2-(chloromethyl)-8-methylimidazo[1,2-a]pyridine</strong> (Example 54, Step 1; 0.294 g), 1-(2,4-dichlorophenyl)piperazine (Example 31, Step 1; 0.396 g) diisopropylethylamine (0.35 mL), and THF (2 mL) is heated at 75 C. for 5 hours. The mixture is then concentrated under reduced pressure, partitioned between saturated aq. sodium bicarbonate and dichloromethane, and the combined organic layers are dried with MgSO4 and concentrated under reduced pressure. The residue is chromatographed on silica gel using methanol/dichloromethane (4/96) and the appropriate fractions are combined and concentrated to give 2-[[4-(2,4-dichlorophenyl)-1-piperazinyl]methyl]-8-methylimidazo[1,2-a]pyridine.

Reference： [1]Patent: US5912246,1999,A

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H200	Unstable explosive
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H202	Explosive; severe projection hazard
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H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 182181-42-6 ]

Quality Control of [ 182181-42-6 ]

Related Doc. of [ 182181-42-6 ]

Product Details of [ 182181-42-6 ]

Calculated chemistry of of [ 182181-42-6 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 182181-42-6 ]

Application In Synthesis of [ 182181-42-6 ]

[ 182181-42-6 ] Synthesis Path-Upstream 1~1

[ 182181-42-6 ] Synthesis Path-Downstream 1~5

Related Functional Groups of [ 182181-42-6 ]

Chlorides

Related Parent Nucleus of [ 182181-42-6 ]

Other Aromatic Heterocycles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 182181-42-6 ]

Related Parent Nucleus of
[ 182181-42-6 ]