[ CAS No. 17286-47-4 ] {[proInfo.proName]}

Name: 17286-47-4|2-(1H-Imidazol-2-yl)ethanamine dihydrochloride|98%
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SKU: A257997
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Quality Control of [ 17286-47-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 17286-47-4 ]

SDS Specification

Alternatived Products of [ 17286-47-4 ]

Product Details of [ 17286-47-4 ]

CAS No. :	17286-47-4	MDL No. :	MFCD08668396
Formula :	C₅H₁₁Cl₂N₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YBIQGKPICKGYRI-UHFFFAOYSA-N
M.W :	184.07	Pubchem ID :	13170812
Synonyms :

Calculated chemistry of [ 17286-47-4 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.4
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	45.0
TPSA :	54.7 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.7 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	1.02
Log Po/w (WLOGP) :	1.51
Log Po/w (MLOGP) :	-0.21
Log Po/w (SILICOS-IT) :	0.86
Consensus Log Po/w :	0.64

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.86
Solubility :	2.53 mg/ml ; 0.0137 mol/l
Class :	Very soluble
Log S (Ali) :	-1.76
Solubility :	3.21 mg/ml ; 0.0174 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.62
Solubility :	4.37 mg/ml ; 0.0238 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.54

Safety of [ 17286-47-4 ]

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

Application In Synthesis of [ 17286-47-4 ]

* 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.

Upstream synthesis route of [ 17286-47-4 ]
Downstream synthetic route of [ 17286-47-4 ]

[ 17286-47-4 ] Synthesis Path-Upstream 1~1

1
[ 88883-77-6 ]
[ 17286-47-4 ]

Reference： [1] Archiv der Pharmazie, 1984, vol. 317, # 1, p. 9 - 14

[ 17286-47-4 ] Synthesis Path-Downstream 1~10

1
[ 75-15-0 ]
[ 17286-47-4 ]
[ 92095-61-9 ]

Reference： [1]Chemische Berichte,1984,vol. 117,p. 2597 - 2614

2
[ 17286-47-4 ]
[ 10191-60-3 ]
[ 92125-35-4 ]

Reference： [1]Chemische Berichte,1984,vol. 117,p. 2597 - 2614

3
[ 17286-47-4 ]
[ 530-62-1 ]
[ 92095-34-6 ]

Reference： [1]Chemische Berichte,1984,vol. 117,p. 2597 - 2614

4
[ 88883-77-6 ]
[ 17286-47-4 ]

Reference： [1]Archiv der Pharmazie,1984,vol. 317,p. 9 - 14

5
C₂₃H₂₇IN₂O₅ [ No CAS ]
[ 17286-47-4 ]
[ 1415657-86-1 ]

Reference： [1]Journal of Organic Chemistry,2012,vol. 77,p. 11079 - 11090

6
[ 17286-47-4 ]
[ 355397-64-7 ]
2,3-bis(4-fluorophenyl)-N-[2-(1H-imidazol-2-yl)ethyl]quinoxaline-6-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44%		To a solution of 2,3-bis(4-fluorophenyl)quinoxaline-6-carboxylic acid (6.00 g, 16.6 mmol) and DIPEA (8.56 g, 66.4 mmol) in DMF (100 mL) was added HATU (9.46 g, 24.9 mmol) at 0 C. After it was stirred for 30 min at 0 C, [2-(lH-imidazol-2-yl)ethyl]amine dihydrochloride (3.34 g, 18.2 mmol) was added to the mixture. The mixture was stirred at 25-30 C for 16 h. Then, NaOH (20% in water, 60 mL) was added to the reaction mixture and it was stirred for 0.5 h at 25 C. The mixture was diluted with H20 (300 mL) and the suspension was filtered. The filter cake was washed with H20 (100 mL x3) and dried in vacuo to give the crude product. It was washed with petroleum ether EtOAc (2/1, 300 mL) and then recrystallized from DMSO/H20 (80 mL/1600 mL) to give yellow solid. The obtained solid was dissolved in THF (100 mL), EtOAc (100 mL) and DMF (100 mL). The insoluble material was removed by filtration, and poured into sat. NaHC03 aq. and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over MgS04 and concentrated in vacuo. The resultant solid was washed with EtOH to give a white solid. A solution of obtained solid in DMSO (60 mL) was added dropwise to ice-cooled water (500 mL). The mixture was stirred at 0 C for 30 min. The precipitate was collected by filtration, and washed with cold water and dried in vacuo to give 2,3-bis(4- fluorophenyl)-N-[2-(lH-imidazol-2-yl)ethyl]quinoxaline-6-carboxamide (3.35 g, 44%) as off-white solid. LCMS (ESI+): m/z = 456.1 (Mu+Eta). H NMR (300 MHz, OMSO-d6) delta 2.84-3.06 (m, 2 H), 3.52- 3.77 (m, 2 H), 6.91 (s, 2 H), 7.08-7.35 (m, 4 H), 7.43-7.72 (m, 4 H), 8.09-8.39 (m 2 H), 8.66 (d, J= 1.5 Hz, 1 H), 9.03 (t, J= 5.5 Hz, 1 H), 11.85 (br s, 1H).

Reference： [1]Patent: WO2015/161142,2015,A1 .Location in patent: Paragraph 00285

7
2-chloro-3-(4-fluorophenyl)quinoxaline-6-carbonyl chloride [ No CAS ]
[ 17286-47-4 ]
2-chloro-3-(4-fluorophenyl)-N-[2-(1H-imidazol-2-yl)ethyl]quinoxaline-6-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With triethylamine; In N,N-dimethyl acetamide; at 20℃;	To a suspension of 2-chloro-3-(4-fluorophenyl)quinoxaline-6-carbonyl chloride (0.250 g, 0.778 mmol) (prepared similarly to Example 3, step 6, or Example 27, step 6) and [2-(lH-imidazol-2- yl)ethyl]amine dihydrochloride (172 mg, 0.934 mmol) in DMA (16.9 mL, 182 mmol) was added triethylamine (0.542 mL, 3.89 mmol). The homogeneous reaction mixture was stirred at rt overnight. The reaction mixture was diluted with EtOAc and sat.NaHC03. The NaHC03layer was extracted with EtOAc. The combined EtOAc layers were washed with water and evaporated to dryness, triturated with small amount of CH3CN and water to give 2-chloro-3-(4-fluorophenyl)-N-[2-(lH-imidazol-2- yl)ethyl]quinoxaline-6-carboxamide (280 mg, 91%) as a white solid. LCMS (ESI+): m/z = 396.1 (Mu+Eta).

Reference： [1]Patent: WO2015/161142,2015,A1 .Location in patent: Paragraph 00356

8
2-chloro-3-(4-fluorophenyl)quinoxaline-6-carbonyl chloride [ No CAS ]
[ 17286-47-4 ]
N-(2-(1H-imidazol-2-yl)ethyl)-3-chloro-2-(4-fluorophenyl)quinoxaline-6-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%	With triethylamine; In N,N-dimethyl acetamide; at 20℃;	To a mixture of 3 -chloro-2-(4-fluorophenyl)quinoxaline-6-carbonyl chloride ( 1.03 g, 3.21 mmol, prepared according to Example 44, Route 1, Step 3) in N,N-dimethylacetamide (45 mL) was added 2-(lH-imidazol-2-yl)ethanamine dihydrochloride (709 mg, 3.85 mmol) and TEA (2.24 mL, 16.1 mmol) and the resulting mixture was stirred at room temperature overnight. The reaction was then poured into saturated sodium bicarbonate (50 mL). Water (50 mL) and ethyl acetate (200 mL) were added. The layers were separated and the aquous layer was extracted with ethyl acetate (100 mL). The combined organic layers were washed with water (5 x 50 mL), dried, filtered and concentrated in vacuo. Silica gel chromatography gave N-(2-( 1 H-imidazol-2-yl)ethyl)-3 -chloro-2-(4-fluorophenyl)quinoxaline-6- carboxamide (541 mg, 42%). LCMS (ESI+): m/z = 396.1 (M+H). H NMR (400 MHz, OMSO-d6) delta 11.86 (bs, 1H), 9.06 (t, J= 5.6 Hz, 1 H), 8.55 (d, J= 1.6 Hz, 1 H), 8.30 (dd, J= 8.8, 1.6 Hz, 1 H), 8.27 (d, J= 8.8 Hz, 1 H), 7.96-7.93 (m, 2 H), 7.45-7.40 (m, 2 H), 6.92 (bs, 2 H), 3.68-3.62 (m, 2 H), 2.97-2.93 (m, 2 H).

Reference： [1]Patent: WO2015/161142,2015,A1 .Location in patent: Paragraph 00413

9
1-(4-chloro-6-methylpyrimidin-2-yl)-3-(naphthalen-2-yl)urea [ No CAS ]
[ 17286-47-4 ]
1-(4-((2-(1H-imidazol-2-yl)ethyl)amino)-6-methylpyrimidin-2-yl)-3-(naphthalen-2-yl)urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	With triethylamine; In isopropyl alcohol; at 80℃;	1-(4-Chloro-6-methylpyrimidin-2-yl)-3-(naphthalen-2-yl)urea (2) (75 mg, 0.23 mmol) was suspended in 2-propanol (0.48 mL). To this was added triethylamine (0.05 mL, 0.36 mmol) and then N,N?-dimethyl-1,3-propanediamine (0.04 mL, 0.28 mmol), and the mixture was heated at 80oC with stirring overnight. Upon cooling, the mixture was diluted with ethanol (3 mL) and the precipitate formed was filtered to give the title compound (3) (55 mg, 61%). LC/MS: Method 1: Rt = 0.36 min, m/z = 379.3 [MH+]. 1-(4-((2-(1H-Imidazol-2-yl)ethyl)amino)-6-methylpyrimidin-2-yl)-3-(naphthalen-2- yl)urea (22) was prepared by a similar procedure as for example 1 using 3-(1H-imidazol-2-yl)- ethylamine dihydrochloride except the final product was purified by preparative TLC using 20% 1M NH4OH in MeOH/80% DCM. (13.0 mg, 21%). LC/MS: Rt = 1.62 min, m/z = 388.2 [MH+].

Reference： [1]Patent: WO2018/39621,2018,A1 .Location in patent: Paragraph 00301-00302; 00304

10
4-bromo-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid [ No CAS ]
[ 17286-47-4 ]
N-(2-(1H-imidazol-2-yl)ethyl)-4-bromo-1H-pyrrolo[2,3-b]pyridine-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		A mixture of 4-bromo-lH-pyrrolo[2,3-b]pyridine-2-carboxylic acid(200 mg, 0.830 mmol) in DMF (15 mL) was added hydroxybenzotriazole (HOBt) (224 mg, 1.66 mmol), EDOHC1 (318 mg, 1.66 mmol), TEA (420 mg, 4.15 mmol, 0.58m), the reaction mixture was stirred at 50 C for 0.5 hour, then added 2-(lH-imidazol-2-yl) ethanamine (305 mg, 1.66 mmol, 2 HC1 salt) into it and continued stirred for another 2.5 h to give a pale yellow suspension. LCMS showed the purity of the desired product (Rt = 0.600 min; MS Calc?d: 333.0; MS Found: 333.9 [M+H]+). The mixture was diluted with water (15 mL), then extracted with EtOAc (20 mL x2), the combined extracts was washed with brine (25 mL x2), dried over Na2S04, filtered and concentrated under reduced pressure to give N-(2-(lH-imidazol-2- yl)ethyl)-4-bromo-lH-pynOlo[2,3-b]pyridine-2-carboxamide (250 mg, purity: 92%, yield: 83%) as an off-white solid NMR (400 MHz, DMSO-r e) d 2.86-2.95 (2H, m), 3.52-3.65 (2H, m), 6.85-6.98 (2H, m), 7.15 (1H, s), 7.42 (1H, d, J= 5.2 Hz), 8.19 (1H, d, J= 4.8 Hz), 8.83 (1H, br s), 11.82 (1H, br s), 12.56 (1H, br s).

Reference： [1]Patent: WO2019/126733,2019,A1 .Location in patent: Paragraph 0587

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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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Health hazards
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H316	Causes mild skin irritation
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H318	Causes serious eye damage
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Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
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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. 17286-47-4 ] {[proInfo.proName]}

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Calculated chemistry of [ 17286-47-4 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 17286-47-4 ]

Application In Synthesis of [ 17286-47-4 ]

[ 17286-47-4 ] Synthesis Path-Upstream 1~1

[ 17286-47-4 ] Synthesis Path-Downstream 1~10

Related Functional Groups of [ 17286-47-4 ]

Amines

Related Parent Nucleus of [ 17286-47-4 ]

Imidazoles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 17286-47-4 ]

Related Parent Nucleus of
[ 17286-47-4 ]