[ CAS No. 66247-84-5 ]

Name: (1H-Imidazol-4-yl)methanamine hydrochloride
Brand: Ambeed
SKU: A241837
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COA GC NMR CNMR HPLC/UPLC LC-MS SDS

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Product Details of [ 66247-84-5 ]

CAS No. :	66247-84-5	MDL No. :	MFCD13176517
Formula :	C₄H₈ClN₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	133.58	Pubchem ID :	45791344
Synonyms :

Computed Properties of [ 66247-84-5 ]

TPSA :Topological Polar Surface Area	54.7	H-Bond Acceptor Count :	2
XLogP3 :	-	H-Bond Donor Count :	3
SP3 :	0.25	Rotatable Bond Count :	1

Safety of [ 66247-84-5 ]

Signal Word:	Warning	Class	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 66247-84-5 ]

Upstream synthesis route of [ 66247-84-5 ]
Downstream synthetic route of [ 66247-84-5 ]

[ 66247-84-5 ] Synthesis Path-Upstream 1~4

1
[ 3034-50-2 ]
[ 66247-84-5 ]

Yield	Reaction Conditions	Operation in experiment
100%	Stage #1: With ammonia In methanol at 40℃; for 0.50 h; Stage #2: With hydrogen In methanol at 40 - 50℃; for 28.00 h; Stage #3: With hydrogenchloride In methanol; diethyl ether	12.0 g (124 mmol) 4-formyl-imidazole are placed together with 750 mg Raney nickel in 1000 ml of methanolic ammonia solution and shaken at 40° C. for 30 min. Then the mixture is hydrogenated in a Parr apparatus under a hydrogen atmosphere at 5 bars pressure at 40° C. for 14 h. Another 750 mg Raney nickel are then added and the mixture is again hydrogenated at 50° C. under a hydrogen atmosphere at 5 bars pressure for 14 h. The mixture is filtered, evaporated down i. vac., and in each case methanol, toluene and ethanol are added to the residue and it is again evaporated down completely i. vac. The residue is combined with ethereal hydrochloric acid in methanol and evaporated down completely i. vac. The residue is in each case combined with methanol and dichloromethane and evaporated down completely i. vac.Yield: 21.2 g (quant.)R_tvalue: 0.49 min (D)C₄H₇N₃*2 HCl (170.04/97.12)Mass spectrum: (M+H)⁺=98

Reference： [1] Patent: US2008/51578, 2008, A1. Location in patent: Page/Page column 34

2
[ 1225653-08-6 ]
[ 66247-84-5 ]

Yield	Reaction Conditions	Operation in experiment
29%	With hydrogenchloride; hydrogen In tetrahydrofuran; ethanol; ethyl acetate at 80℃; for 3.00 h;	18-1-3 C-(1 H-lmidazol-4-yl)methylamine dihydrochloride; To a solution containing 450 mg of piperidin-1 -yl-(1 -trityl-1 H-imidazol-4-yl- methylene)amine in 3.5 mL of 3N hydrogen chloride in ethyl acetate are added 90 mg of 10percent Pd/C, 0.5 mL of THF and 0.9 mL of ethanol. The reaction medium is placed under a hydrogen pressure of 6 bar and heated at 80°C for 3 hours. After filtering off the catalyst and evaporating off the solvents, the crude product obtained is chromatographed on silica gel (eluent: 6/4 DCIWMeOH). 50 mg of C-(1 H-imidazol- 4-yl)methylamine dihydrochloride in the form of a white powder are obtained in a yield of 29percent.

Reference： [1] Patent: WO2010/52255, 2010, A1. Location in patent: Page/Page column 68

3
[ 191104-34-4 ]
[ 66247-84-5 ]

Reference： [1] Heterocycles, 1994, vol. 37, # 1, p. 275 - 282

4
[ 57090-90-1 ]
[ 66247-84-5 ]

Reference： [1] Journal of the American Chemical Society, 1949, vol. 71, p. 2801

[ 66247-84-5 ] Synthesis Path-Downstream 1~10

1
[ 728034-12-6 ]
[ 66247-84-5 ]
[ 165806-95-1 ]
4-(1-((1H-imidazol-4-yl)methyl)-4-(4-fluorophenyl)-1H-imidazol-5-yl)-1H-pyrrolo[2,3-b]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%		General procedure: To a solutionof the corresponding aldehyde (1.2 eq.; unless stated otherwise) in DMF (2 inL per 0.3 mmol of aldehyde; unless stated otherwise) was added the corresponding amine (2.5 eq.; unless stated otherwise) and the resulting solution was stirred at 25 C to form the corresponding inline. Then, the corresponding isocyano(tosyl)methyl)arene reagent (1 eq.; unless stated otherwise) and K2CO3 (1.5 eq.; unless stated otherwise) were added and the reaction mixture was stirred at 25 C (unless stated otherwise). The reaction was stopped after the time indicated for each particular reaction. The reaction progress was monitored by TLC. (0083) A saturated aqueous solution of NH4CI (10 mL per 1 mmol of aldehyde) was added to the reaction mixture, which was then extracted with EtOAc (2 x 30 mL per 1 mmol of aldehyde). The combined organic extracts were washed with H2O (2 x 25 mL per 1 mmol of aldehyde), dried over MgSCC, filtered, and the solvent was evaporated in vacuo to provide the crude product. The residue obtained after the workup was purified using column chromatography or preparative TLC (unless stated otherwise). (0084) note: in cases when the amine was used as HC1 salt, 4 eq. of K2CO3 were used

Reference： [1]Patent: WO2019/185631,2019,A1.Location in patent: Page/Page column 14; 82-83

2
2-chloro-4-((2-fluoro-6-(trifluoromethyl)benzyl)amino)quinazoline-8-carbonitrile [ No CAS ]
[ 66247-84-5 ]
2-(((1H-imidazol-4-yl)methyl)amino)-4-((2-fluoro-6-(trifluoromethyl)benzyl)amino)quinazoline-8-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56.6%	With N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; at 100℃; for 16h;	N,N-Diisopropylethylamine (0.24 mL, 1.389 mmol) was added to 2-chloro-4-((2-fluoro-6-(trifluoromethyl)benzyl)amino)quinazoline-8-carbonitrile 4 (105.8 mg, 0.278 mmol) in 1,4-dioxane (1.3 mL) and dimethyl sulfoxide (1.3 mL) at room temperature, followed by<strong>[66247-84-5](1H-imidazol-4-yl)methanamine dihydrochloride</strong> 5d (71 mg,0.417 mmol) and the solution was heated to 100 °C and stirred forsixteen hours. The reaction mixture was poured into ether, washed with water, dried over magnesium sulfate, filtered, and concentrated.The residue was purified by silica gel chromatography,eluting with methanol:ethyl acetate (1:24) to give 2-(((1H-imidazol-4-yl)methyl)amino)-4-((2-fluoro-6-(trifluoromethyl)benzyl)amino)quinazoline-8-carbonitrile 6d (73.1 mg, 0.157 mmol, 56.6percentyield). 1H NMR (400 MHz, CD3SOCD3) d 11.82 (br s, 0.6H), 11.71(br s, 0.4H), 8.38?8.14 (m, 2H), 8.02?7.92 (m, 1H), 7.70?6.80 (m,7H), 4.86?4.68 (m, 2H), 4.51 (d, 0.8H, J = 6 Hz), 4.45 (d, 1.2H, J = 6Hz); LC?MS (LC?ES) M+H = 442.

Reference： [1]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 2107 - 2150

3
4-(2,4-difluorophenoxy)-3-(7-methoxy-1-methyl-1H-pyrrolo[2,3-c]pyridin-3-yl)benzaldehyde [ No CAS ]
[ 66247-84-5 ]
N-((1H-imidazol-4-yl)methyl)-1-(4-(2,4-difluorophenoxy)-3-(7-methoxy-1-methyl-1H-pyrrolo[2,3-c]pyridin-3-yl)phenyl)methanamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%		Example 119A N-((1H-imidazol-4-yl)methyl)-1-(4-(2,4-difluorophenoxy)-3-(7-methoxy-1-methyl-1H-pyrrolo[2,3-c]pyridin-3-yl)phenyl)methanamine [1125] To a suspension of <strong>[66247-84-5]1H-imidazol-4-ylmethylamine dihydrochloride</strong> (269 mg, 1.59 mmol) in a mixture of dichloromethane (3 mL) and methanol (1 mL) was added triethylamine (0.442 mL, 3.17 mmol). After stirring the mixture for five minutes, Example 105B (125 mg, 0.317 mmol) and acetic acid (0.181 mL, 3.17 mmol) were added. The mixture was heated at 50° C. for 1 hour. The mixture was cooled in an ice bath and sodium triacetoxyborohydride (134 mg, 0.634 mmol) was added portionwise over several minutes. After 15 minutes, the ice bath was removed and the reaction mixture was stirred 2 hours while warming to ambient temperature. The reaction mixture was quenched with 1 M sodium hydroxide (2 mL) and partitioned between saturated aqueous sodium bicarbonate solution (50 mL) and ethyl acetate (50 mL). The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by flash column chromatography (silica gel, 0-10percent 7N methanolic ammonia in methylene chloride) to provide the title compound (90.3 mg, 62percent yield).

Reference： [1]Patent: US2014/275026,2014,A1.Location in patent: Paragraph 1125

4
[ 191104-34-4 ]
[ 66247-84-5 ]

Reference： [1]Heterocycles,1994,vol. 37,p. 275 - 282

5
[ 57090-90-1 ]
[ 66247-84-5 ]

Reference： [1]Journal of the American Chemical Society,1949,vol. 71,p. 2801

6
[ 1225653-08-6 ]
[ 66247-84-5 ]

Yield	Reaction Conditions	Operation in experiment
29%	With hydrogenchloride; hydrogen;palladium 10% on activated carbon; In tetrahydrofuran; ethanol; ethyl acetate; at 80℃; under 4500.45 Torr; for 3h;	18-1-3 C-(1 H-lmidazol-4-yl)methylamine dihydrochloride; To a solution containing 450 mg of piperidin-1 -yl-(1 -trityl-1 H-imidazol-4-yl- methylene)amine in 3.5 mL of 3N hydrogen chloride in ethyl acetate are added 90 mg of 10percent Pd/C, 0.5 mL of THF and 0.9 mL of ethanol. The reaction medium is placed under a hydrogen pressure of 6 bar and heated at 80°C for 3 hours. After filtering off the catalyst and evaporating off the solvents, the crude product obtained is chromatographed on silica gel (eluent: 6/4 DCIWMeOH). 50 mg of C-(1 H-imidazol- 4-yl)methylamine dihydrochloride in the form of a white powder are obtained in a yield of 29percent.

Reference： [1]Patent: WO2010/52255,2010,A1.Location in patent: Page/Page column 68

7
[ 1225591-94-5 ]
[ 66247-84-5 ]
[ 1225653-10-0 ]

Yield	Reaction Conditions	Operation in experiment
63%	With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 80℃; for 2h;	78-2 Methyl (S)-2-[3-(1H-imidazol-4-yl-methyl)ureido]-3-(4-methoxyphenyl)- propanoate; 1 .1 g (0.37 mmol) of methyl (S)-3-(4-methoxyphenyl)-2-(4-nitrophenoxycarbonyl- amino)propanoate (cf. preparation 2-2) and 0.7 mL (0.37 mmol) of diisopropyl- ethylamine in 5 mL of dimethylformamide are added at 800C to a solution of 500 mg (0.37 mmol) of C-(1 H-imidazol-4-yl)methylamine dihydrochloride in 15 mL of dimethylformamide. The reaction mixture is stirred for 2 hours at 800C. The reaction is stopped by adding 30 ml. of water and then extracted with ethyl acetate. The organic phases are combined and dried over sodium sulfate. The solvents are evaporated off and the residue is then chromatographed on silica gel (eluent: 80/20 dichloromethane/methanol). 279 mg of methyl (S)-2-[3-(1 H-imidazol-4-yl-methyl)- ureido]-3-(4-methoxyphenyl)propanoate in the form of a yellow oil are obtained in a yield of 63percent.

Reference： [1]Patent: WO2010/52255,2010,A1.Location in patent: Page/Page column 68-69

8
[ 66247-84-5 ]
[ 129451-79-2 ]
[ 1093660-15-1 ]

Reference： [1]European Journal of Organic Chemistry,2008,p. 4915 - 4923

9
[ 1076192-10-3 ]
[ 66247-84-5 ]
[ 1076192-11-4 ]

Yield	Reaction Conditions	Operation in experiment
50%	With caesium carbonate; In N,N-dimethyl-formamide; at 60℃; for 3h;	To the previous mixture containing intermediate a115 (0.44 g, 1.15 mmol, 73 wt percent) is added (1 /-/-imidazol-4-ylmethyl)amine dihydrochloride (0.59 g, 3.46 mmol, 3 eq) [from A. Turner et al., J. Am. Chem. Soc. (1949), 71 , 2801-2803.], and anhydrous cesium carbonate (1.88 g, 5.76 mmol, 5 eq) in dry DMF (15 ml_). The mixture is vigorously stirred at 60 0C for 3 h. The reaction mixture is cooled, concentrated under reduced pressure, diluted with water, and subjected to extraction with ethyl acetate (three times). The combined organic extracts are washed with brine, dried over anhydrous Na2SC>4, and evaporated. The residue (0.35 g) is purified by chromatography on silicagel (gradient CHCI3/MeOH from 20/1 to 10/1 v/v) to afford 5-chloro-2-(1 H-imidazol-4-ylmethyl)-1 ,4- dihydroisoquinolin-3(2H)-one 53 (0.15 g). Yield: 50 percent. LC-MS (MH+): 262/264.

Reference： [1]Patent: WO2008/132139,2008,A2.Location in patent: Page/Page column 94-95

10
[ 771-50-6 ]
[ 66247-84-5 ]
N-[(1H-Imidazol-4-yl)methyl]-1H-indole-3-carboxamide hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride; triethylamine; In methanol; 1,2-dichloro-ethane; acetonitrile;	EXAMPLE 1 N-[(1H-Imidazol-4-yl)methyl]-1H-indole-3-carboxamide hydrochloride A suspension of indole-3-carboxylic acid (0.592 g) and thionyl chloride (0.6 ml) in 1,2-dichloroethane (50 ml) was stirred at room temperature for 60h under nitrogen. The suspension was evaporated in vacuo and further 1,2-dichloroethane (50 ml) was added. The suspension was re-evaporated to give a solid (0.6 g) which was dissolved in acetonitrile (25 ml) and triethylamine (5 ml), and added to a stirred suspension of <strong>[66247-84-5]imidazole-4-methanamine dihydrochloride</strong> (0.684 g) and triethylamine (5 ml) in acetonitrile (25 ml) at -5° under nitrogen. The reaction was stirred for 1h while warming to room temperature and then heated at reflux for 20h. The mixture was evaporated in vacuo, dissolved in methanol (20 ml) and partitioned between hydrochloric acid (0.2N; 2200 ml) and dichloromethane (2100 ml). The combined aqueous layers were basified with saturated potassium carbonate and extracted with chloroform (3*150 ml). The combined chloroform layers were dried and evaporated in vacuo to give a semi-solid which was triturated with ether to give a solid (0.24 g). This was adsorbed onto silica and purified by FCC eluding with System A (83.5:151.5) to give a solid (ca. 50 mg) which was dissolved in methanol (3 ml) and acidified with ethanolic hydrogen chloride. Dry ether (20 ml) was added until the solution turned cloudy, precipitating the title compound (26 mg), m.p. 225°-229° (decomp.). Analysis Found: C,55.1; H,4.7; N,19.5; C13 H12 N4 O. HCl. 0.38H2 O requires C,55.1; H,4.5; N,19.5percent

Reference： [1]Patent: US5026722,1991,A

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Ghs Precautionary Statements

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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
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Health hazards
Code	Phrase
H300	Fatal if swallowed
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H302	Harmful if swallowed
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H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
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. 66247-84-5 ]

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[ 66247-84-5 ] Synthesis Path-Upstream 1~4

[ 66247-84-5 ] Synthesis Path-Downstream 1~10

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Amines

Related Parent Nucleus of [ 66247-84-5 ]

Imidazoles

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[ 66247-84-5 ]

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[ 66247-84-5 ]