[ CAS No. 63286-28-2 ] {[proInfo.proName]}

Name: 63286-28-2|2-Chloro-3-hydrazinylpyrazine|98%
Brand: Ambeed
SKU: A562796
Price: 7.0 USD
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Quality Control of [ 63286-28-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 63286-28-2 ]

SDS Specification

Alternatived Products of [ 63286-28-2 ]

Product Details of [ 63286-28-2 ]

CAS No. :	63286-28-2	MDL No. :	MFCD08272804
Formula :	C₄H₅ClN₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PUUGNIKJWZNTBK-UHFFFAOYSA-N
M.W :	144.56	Pubchem ID :	321430
Synonyms :

Calculated chemistry of [ 63286-28-2 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	34.25
TPSA :	63.83 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.96 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.93
Log Po/w (XLOGP3) :	0.31
Log Po/w (WLOGP) :	0.22
Log Po/w (MLOGP) :	-0.49
Log Po/w (SILICOS-IT) :	0.21
Consensus Log Po/w :	0.24

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.36
Solubility :	6.33 mg/ml ; 0.0438 mol/l
Class :	Very soluble
Log S (Ali) :	-1.21
Solubility :	8.85 mg/ml ; 0.0612 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.94
Solubility :	1.67 mg/ml ; 0.0115 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.36

Safety of [ 63286-28-2 ]

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P280-P301+P310+P330-P302+P352-P305+P351+P338+P310	UN#:	2811
Hazard Statements:	H301-H315-H318-H335	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 63286-28-2 ]

* 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 [ 63286-28-2 ]
Downstream synthetic route of [ 63286-28-2 ]

[ 63286-28-2 ] Synthesis Path-Upstream 1~5

1
[ 4858-85-9 ]
[ 63286-28-2 ]

Yield	Reaction Conditions	Operation in experiment
96%	With hydrazine hydrate In ethanol; waterReflux	Step 1 : To a solution of 2,3-dichloropyrazine (150 g, 1 .01 mol) in EtOH (700 mL) was added hydrazine monohydrate (124.53g, 2.11 mmol, 85percent in water). The reaction mixture was heated under reflux overnight. The reaction mixture was cooled and the precipitate was filtered. The resulting solid was washed with water (100 mL, two times), then cold EtOH (150 ml, two times) and dried under reduced pressure to give the 2-chloro-3-hydrazinylpyrazine (140 g, yield 96percent) .
93%	With hydrazine In ethanol at 80℃; for 1 h;	2,3-Dichloropyrazine A-1 (15 g; 100.68 mmol) and hydrazine hydrate 65percent (15.509 ml; 201.37 mmol) are dissolved in 45 ml ethanol and stirred for 1 h at 80° C. While cooling down, a precipitate is formed. It is slurred up with a small amount of water and filtered off. It is washed with water and then dried to afford the product. Yield: 93percent (13.6 g; 94.07 mmol); HPLC-MS: (M+H)⁺=145/147; t_Ret=0.34 min; method FECB5.
93%	With hydrazine hydrate In ethanol at 80℃; for 1 h;	2,3-Dichloropyrazine A-1 (15 g; 100.68 mmol) and hydrazine hydrate 65percent (15.509 ml; 201.37 mmol) are dissolved in 45 ml ethanol and stirred for 1 h at 80° C. While cooling down, a precipitate is formed. It is slurred up with a small amount of water and filtered off. It is washed with water and then dried to afford the product. Yield: 93percent (13.6 g; 94.07 mmol) HPLC-MS: (M+H)⁺=145/147; t_Ret=0.34 min; method FECB5

90%	With hydrazine hydrate In ethanolReflux; Inert atmosphere; Large scale	2,3-dichloropyrazine (1000 g, 6.7 mol) and hydrazine monohydrate (700 g, 14 mol) were dissolved in absolute ethanol (2 L) and refluxed under N₂ overnight. A crystalline precipitate formed, which was collected by filtration, washed with ethanol (1 L), and dried to afford the desired produced as a yellow solid (880 g, 90percent yield).
88%	at 60℃; for 3 h;	[00114] 2,3-Dichloropyrazine (25 g) and anhydrous hydrazine (21 ml) were dissolved in pyridine (100 mL) and heated to 60 ⁰C. After 3h, the reaction was concentrated in vacuo to yield a residue. The residue was rinsed with water and the filtered. The resulting solid was collected by filtration and dried at 40 ⁰C in vacuo to afford Compound IA as a light yellow solid (20.3 g, 88percent).
87%	With hydrazine hydrate In ethanol for 3 h; Reflux	A 100 mL round bottom flask was charged with 2,3-dichloropyrazine (10 g, 67.6 mmol), hydrazine hydrate (6.76 g, 135 mmol) and ethanol (40 mL). The resulting mixture was stirred at reflux for 3 h. Reaction progress was monitored by TLC (EtO Ac/petroleum ether = 2:1). Work-up: the reaction mixture was cooled to room temperature. The solid was collected by filtration, washed with water (30 mL x 2) and dried, to afford 8.4 g (87percent) of the product as a yellow solid.
85%	With hydrazine In ethanol for 1.5 h; Reflux	Hydrazine hydrate (20 mL, 43.6 mmol) was slowly added dropwise to a solution of 2,3-dichloropyrazine (3.2 g, 21.8 mmol) in ethanol (600 mL).The temperature was raised to reflux for 1.5 hours, and the mixture was dried under reduced pressure.The solid is added to the water and filtered.The solid was recrystallized twice in ethanol to give a yellow solid(2.68 g, yield 85percent).
80%	With hydrazine hydrate In ethanol for 3 h; Reflux	STEP1 Preparation of 2-chloro-3-hydrazinylpyrazine To a solution of 2,3-dichloropyrazine (10.0 g, 67.1 mmol) in EtOH (224 mL) was added hydrazine hydrate (6.72 g, 134 mmol) at room temperature. The reaction mixture was refluxed for 3 hours. A precipitated solid was collected by filtration, washed with EtOH and dried under vacuum to afford 2-chloro-3-hydrazinylpyrazine (7.80 g, 80percent) as an orange solid. ¹H-NMR (DMSO-d₆, 400 MHz): δ 8.30 (1H, brs), 8.07 (1H, d, J=2.4 Hz), 7.57 (1H, d, J=2.8 Hz), 4.34 (2H, brs).
74%	With hydrazine hydrate In ethanol for 1 h; Reflux	2,3-dichloro-pyrazine (25 g) was dissolved in ethanol (500 mL),Hydrazine monohydrate (16.7 mL) was added, And the mixture was stirred under reflux for 1 hour and a half. Water was added to the reaction solution, and the precipitated solid was dried under reduced pressure after filtering off the resulting solid to give the title compound as white crystals by recrystallization from ethanol (18.12g, 74percent).
73%	With hydrazine In ethanol	2,3-Dichloropyrazine (2 mL, 13 mmol) was dissolved in 95percent ethanol (4 mL) and to this was added, dropwise and with stirring, hydrazine anhydrous (2 mL, 67 mmol). During the addition of the hydrazine the solution became warm and yellowish. Following cooling of this mixture in an ice bath, the resulting material was isolated by filtration, washed with cold aqueous 95percent ethanol to riled 1-(3-chloropyrazin-2-yl)hydrazine (1.42 g, 73percent yield) as white crystals. No further purification was done. MS m/z: 145.0 (M+1).
59%	With hydrazine In ethanol at 80℃; for 1.5 h;	2,3-Dichloropyrazine (2 g, 13.42 mmol), hydrazine (1.324 g, 26.8 mmol) and ethanol (40 ml) were combined and the reaction mixture was stirred at 80° C. for 1.5 h. The mixture was cooled to room temperature and the yellow flakes were filtered off. The solid was washed with a small amount of water and dried. The mother liquor was concentrated to afford a yellow solid triturated with a small amount of water and dried. The 2 solids were combined to afford title product 471 (1.15 g, 59percent) as yellow solid. MS (m/z): 145.0 (M+H).
13.6 g	With hydrazine hydrate In ethanol for 1 h;	2,3-Dichloropyrazine A-1 (15 g; 100.68 mmol) and hydrazine hydrate 65 percent (15.509 ml; 201.37 mmol) are dissolved in 45 ml ethanol and stirred for 1 h at 80 °C. While cooling down, a precipitate is formed. It is slurred up with a small amount of water and filtered off. It is washed with water and then dried to afford the product. Yield: 93percent (13.6 g; 94.07mmol) HPLC-MS: (M+H)⁺ = 145/147; t_Ret = 0.34 min; method FECB5

Reference： [1] Patent: WO2016/55618, 2016, A1, . Location in patent: Page/Page column 64
[2] Patent: US2014/142098, 2014, A1, . Location in patent: Paragraph 0233 - 0236
[3] Patent: US2015/133447, 2015, A1, . Location in patent: Paragraph 0287; 0288; 0289
[4] Patent: WO2013/39785, 2013, A2, . Location in patent: Page/Page column 80; 81
[5] Patent: WO2008/130951, 2008, A1, . Location in patent: Page/Page column 60
[6] Patent: WO2011/112766, 2011, A2, . Location in patent: Page/Page column 78
[7] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 20, p. 4606 - 4613
[8] Patent: CN108250128, 2018, A, . Location in patent: Paragraph 0775; 0777; 0778; 0779
[9] Patent: US2017/204101, 2017, A1, . Location in patent: Paragraph 0397; 0398
[10] Patent: JP5851663, 2016, B1, . Location in patent: Paragraph 0300
[11] Patent: US2010/120774, 2010, A1, . Location in patent: Page/Page column 37
[12] Patent: US2017/749, 2017, A1, . Location in patent: Paragraph 0708
[13] Asian Journal of Chemistry, 2013, vol. 25, # 7, p. 3660 - 3664
[14] Patent: WO2015/67770, 2015, A1, . Location in patent: Page/Page column 40
[15] Journal of Molecular Structure, 2015, vol. 1100, p. 137 - 144
[16] Journal of Molecular Structure, 2016, vol. 1106, p. 277 - 285
[17] Patent: WO2016/100349, 2016, A2, . Location in patent: Paragraph 0196; 0258
[18] Patent: WO2004/58266, 2004, A1, . Location in patent: Page/Page column 42

2
[ 7461-50-9 ]
[ 63286-28-2 ]

Yield	Reaction Conditions	Operation in experiment
73%	With hydrazine In ethanol; water	2,3-Dichloropyrazine (2 mL, 13 mmol) was dissolved in 95percent ethanol (4 niL) and to this was added, dropwise and with stirring, hydrazine anhydrous (2 mL, 67 mmol). During the addition of the hydrazine the solution became warm and yellowish. Following cooling of this mixture in an ice bath, the resulting material was isolated by filtration, washed with cold aqueous 95percent ethanol to riled l-(3-chloropyrazin-2-yl)hydrazine (1.42 g, 73percent yield) as white crystals. No further purification was done. MS m/z: 145.0 (M+l).

Reference： [1] Patent: WO2009/64418, 2009, A1, . Location in patent: Page/Page column 85

3
[ 122-51-0 ]
[ 63286-28-2 ]
[ 68774-77-6 ]

Yield	Reaction Conditions	Operation in experiment
95%	for 4 h; Reflux	It was stirred for 4 hours at reflux mixture of the compound obtained in Step 1 (8 g) and triethyl orthoformate (32 mL). The reaction solution was cooled to room temperature, the precipitated solid was washed after filtration, with ethanol, To give the title compound followed by drying under reduced pressure (8.10g, 95percent).
62%	for 2 h; Heating / reflux	A mixture of l-(3-chloropyrazin-2-yl)hydrazine (0.90 g, 62 mmol), triethyl orthoformate (2.3 mL), 14 mmol), and dry xylene (15 mL) was refluxed with stirring for 2 h. The mixture was brought to RT, diethyl ether was added and the suspension was filtered. The solid collected was washed with diethyl ether to afford 8-chloro-[l,2,4]triazolo[4,3- ajpyrazine (0.60 g, 62percent yield). MS m/z: 155.0 (M+l).
62%	for 2 h; Reflux	Step 3: 8-chloro-[1,2,4]triazolo[4,3-a]pyrazine A mixture of 1-(3-chloropyrazin-2-yl)hydrazine (0.90 g, 62 mmol), triethyl orthoformate (2.3 mL), 14 mmol), and dry xylene (15 mL) was refluxed with stirring for 2 h. The mixture was brought to RT, diethyl ether was added and the suspension was filtered. The solid collected was washed with diethyl ether to afford 8-chloro-[1,2,4]triazolo[4,3-a]pyrazine (0.60 g, 62percent yield). MS m/z: 155.0 (M+1).

Reference： [1] Patent: JP5851663, 2016, B1, . Location in patent: Paragraph 0301
[2] Patent: WO2009/64418, 2009, A1, . Location in patent: Page/Page column 85
[3] Patent: US2010/120774, 2010, A1, . Location in patent: Page/Page column 37-38

4
[ 63286-28-2 ]
[ 149-73-5 ]
[ 68774-77-6 ]

Yield	Reaction Conditions	Operation in experiment
70%	for 10 h; Reflux	Compound 49A is added to trimethyl orthoformate,The temperature was raised to reflux for 10 hours, cooled to room temperature, and filtered.Obtaining Compound 49B Solid(2 g, yield 70percent).

Reference： [1] Patent: CN108250128, 2018, A, . Location in patent: Paragraph 0775; 0777; 0780; 0781
[2] Journal of Medicinal Chemistry, 2005, vol. 48, # 1, p. 141 - 151

5
[ 78-39-7 ]
[ 63286-28-2 ]
[ 68774-78-7 ]

Yield	Reaction Conditions	Operation in experiment
2 g	Reflux	Step 2: 8-chloro-3-methyl-[l,2,4]triazolo[4,3-a]pyrazine [0197] To a stirred solution of 2-chloro-3-hydrazinylpyrazine (2.0 g, 14 mmol) in xylene (20 mL) was added triethyl orthoformate (5.8 mL, 32 mmol). The mixture was heated under reflux overnight and then cooled to room temperature. The resulting precipitate was collected by filtration to afford the title compound as a brown powder (2.0 g, 87percent). MS (ESI) calcd forC₆H₅CIN₄: 168.0 ; found: 169.2 [M+H]. *H NM (400 MHz, CDCI₃) δ 7.80 (d, J = 4.8 Hz, 1H), 7.71 (d, J = 4.8 Hz, 1H), 2.83 (s, 3H).

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 20, p. 4606 - 4613
[2] Patent: WO2016/100349, 2016, A2, . Location in patent: Paragraph 0197

[ 63286-28-2 ] Synthesis Path-Downstream 1~52

1
[ 50908-31-1 ]
[ 63286-28-2 ]
[ 73012-69-8 ]

Reference： [1]European Journal of Medicinal Chemistry,1979,vol. 14,p. 375 - 380

2
[ 103-72-0 ]
[ 63286-28-2 ]
[ 98792-24-6 ]

Reference： [1]Heterocycles,1985,vol. 23,p. 913 - 925

3
[ 24066-82-8 ]
[ 63286-28-2 ]
[ 98792-20-2 ]

Reference： [1]Heterocycles,1985,vol. 23,p. 913 - 925

4
[ 16182-04-0 ]
[ 63286-28-2 ]
[ 98792-18-8 ]

Reference： [1]Heterocycles,1985,vol. 23,p. 913 - 925

5
[ 38716-29-9 ]
[ 63286-28-2 ]
[ 89578-31-4 ]

Reference： [1]Journal of Medicinal Chemistry,1984,vol. 27,p. 924 - 928

6
[ 16754-56-6 ]
[ 63286-28-2 ]
[ 68797-02-4 ]