[ CAS No. 21279-64-1 ] {[proInfo.proName]}

Name: 21279-64-1|5-Chloropyrazine-2-carboxamide|97%
Brand: Ambeed
SKU: A233666
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Quality Control of [ 21279-64-1 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 21279-64-1 ]

Product Details of [ 21279-64-1 ]

CAS No. :	21279-64-1	MDL No. :	MFCD10686873
Formula :	C₅H₄ClN₃O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	GFEFMHWOSWUJSO-UHFFFAOYSA-N
M.W :	157.56	Pubchem ID :	181450
Synonyms :

Calculated chemistry of [ 21279-64-1 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	35.14
TPSA :	68.87 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) :	-7.62 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.06
Log Po/w (XLOGP3) :	-0.51
Log Po/w (WLOGP) :	0.23
Log Po/w (MLOGP) :	-1.01
Log Po/w (SILICOS-IT) :	0.73
Consensus Log Po/w :	0.1

Druglikeness

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

Water Solubility

Log S (ESOL) :	-0.87
Solubility :	21.1 mg/ml ; 0.134 mol/l
Class :	Very soluble
Log S (Ali) :	-0.47
Solubility :	53.6 mg/ml ; 0.34 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.84
Solubility :	2.25 mg/ml ; 0.0143 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.84

Safety of [ 21279-64-1 ]

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 [ 21279-64-1 ]

* 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 [ 21279-64-1 ]
Downstream synthetic route of [ 21279-64-1 ]

[ 21279-64-1 ] Synthesis Path-Upstream 1~12

1
[ 21279-64-1 ]
[ 89323-09-1 ]

Yield	Reaction Conditions	Operation in experiment
49%	With ammonium hydroxide In methanol at 95℃; for 0.5 h; Microwave irradiation	General procedure: Comp. 1a and 2a were prepared using microwave reactor. Special thick-walled tubes intended for use in microwave reactor were filled with a mixture of corresponding starting comp. 1 or 2 (150 mg, 0.952 mmol), 25percent aqueous ammonia (2 mL, in excess) and MeOH (2 mL). Tubes fitted with stirrer and closed with a special cap were inserted into the reactor. Reaction conditions for microwave-assisted synthesis were: output 200 W, temperature 95 °C, reaction time 30 min using PowerMAX mode.

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 2, p. 450 - 453

2
[ 14508-49-7 ]
[ 77287-34-4 ]
[ 21279-62-9 ]
[ 36070-79-8 ]
[ 21279-64-1 ]

Reference： [1] Collection of Czechoslovak Chemical Communications, 1990, vol. 55, # 10, p. 2493 - 2501
[2] Collection of Czechoslovak Chemical Communications, 1990, vol. 55, # 10, p. 2493 - 2501

3
[ 21279-64-1 ]
[ 36070-75-4 ]

Reference： [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 13, p. 5344 - 5354

4
[ 14508-49-7 ]
[ 77287-34-4 ]
[ 21279-62-9 ]
[ 36070-79-8 ]
[ 21279-64-1 ]

5
[ 33332-25-1 ]
[ 21279-64-1 ]

Yield	Reaction Conditions	Operation in experiment
43%	With trimethylaluminum; ammonium chloride In toluene; benzene at 0 - 50℃;	Production Example 195- [2- (4-hydrazinocarbonylmethylphenyl) ethyl] pyrazine-2- carboxamide dihydrochloride step 1[0129] Ammonium chloride (558 mg, 10.4 iranol) was suspended in benzene (5 ml) and 2M-trimethylaluminum toluene solution (5.2 ml, 10.4 mmol) was added dropwise at 0°C. After stirring for 1 hr, a solution of methyl 5-chloropyrazine-2-carboxylate (600 mg, 3.48 mmol) in benzene (5 ml) was added. The reaction mixture was heated to 50°C, and stirred overnight. After cooling, the reaction mixture was poured into water, and neutralized with saturated aqueous sodium hydrogen carbonate solution. The mixture was extracted with ethyl acetate, and the organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane:methanol = 100:0 -> 98:2) to give 5-chloropyrazine-2-carboxamide (236 mg, yield 43percent) as a white solid.

Reference： [1] Patent: WO2009/145360, 2009, A1, . Location in patent: Page/Page column 71
[2] Patent: EP2123651, 2009, A1, . Location in patent: Page/Page column 21

6
[ 88625-23-4 ]
[ 21279-64-1 ]

Reference： [1] Antimicrobial Agents and Chemotherapy, 1998, vol. 42, # 2, p. 462 - 463
[2] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 2, p. 450 - 453
[3] Journal of Medicinal Chemistry, 2015, vol. 58, # 13, p. 5344 - 5354

7
[ 14508-49-7 ]
[ 77287-34-4 ]
[ 21279-62-9 ]
[ 36070-79-8 ]
[ 21279-64-1 ]

8
[ 34604-60-9 ]
[ 21279-64-1 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 2, p. 450 - 453

9
[ 36070-80-1 ]
[ 21279-64-1 ]

Reference： [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 13, p. 5344 - 5354

10
[ 36070-75-4 ]
[ 21279-64-1 ]

Reference： [1] Agricultural and Biological Chemistry, 1982, vol. 46, # 8, p. 2169 - 2172

11
[ 98-96-4 ]
[ 21279-64-1 ]

Reference： [1] Agricultural and Biological Chemistry, 1982, vol. 46, # 8, p. 2169 - 2172

12
[ 768-36-5 ]
[ 21279-64-1 ]

Reference： [1] Agricultural and Biological Chemistry, 1982, vol. 46, # 8, p. 2169 - 2172

[ 21279-64-1 ] Synthesis Path-Downstream 1~38

1
[ 14508-49-7 ]
[ 77287-34-4 ]
[ 21279-62-9 ]
[ 36070-79-8 ]
[ 21279-64-1 ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1990,vol. 55,p. 2493 - 2501
[2]Collection of Czechoslovak Chemical Communications,1990,vol. 55,p. 2493 - 2501

2
[ 36070-75-4 ]
[ 21279-64-1 ]

Reference： [1]Agricultural and Biological Chemistry,1982,vol. 46,p. 2169 - 2172

3
[ 21279-64-1 ]
[ 74416-17-4 ]

Reference： [1]European Journal of Medicinal Chemistry,1980,vol. 15,p. 157 - 163

4
[ 21279-64-1 ]
[ 735221-62-2 ]

Reference： [1]Agricultural and Biological Chemistry,1982,vol. 46,p. 2169 - 2172

7
[ 88625-23-4 ]
[ 21279-64-1 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonium hydroxide; In dichloromethane; at 20℃; for 2.0h;	General procedure: 5-Chloropyrazine-2-carboxamide (1). 5.0 g of 5-hydroxypyrazine-2-carboxylic acid (0.036 mol) was suspended in 50 mL of dry toluene and treated with thionyl chloride (3 eq., 7.9 mL, 0.108 mol). DMF (10 drops) was added to the reaction mixture as a catalyst. The reaction mixture was heated to reflux for about 1 h. The excess of thionyl chloride was removed by repeated evaporation with dry toluene in vacuo. The crude acyl chloride was dissolved in 50 mL of dichloromethane and excess of aqueous solution of ammonia (m/m, 25%, 10 mL) was added. The mixture was stirred at room temperature for 2 h. Undissolved white product was separated by filtration. Analytical data in accordance to literature. White solid. Yield: 73 %; m.p. 200.1-201.3 C; IR (cm-1) 3407, 3181, 1692; ; 1H NMR (300 MHz, DMSO) delta 8.97 (s, 1H, H3), 8.83 (s, 1H, H6), 8.26 (bs, 1H, CONH2), 7.89 (bs, 1H, CONH2); 13C NMR (75 MHz, DMSO) delta 164.3, 150.8, 144.0, 143.7, 143.3; MS (ESI, Pos.): m/z 157.96 (M+H)+.

Reference： [1]Antimicrobial Agents and Chemotherapy,1998,vol. 42,p. 462 - 463
[2]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 450 - 453
[3]Journal of Medicinal Chemistry,2015,vol. 58,p. 5344 - 5354

8
[ 98-96-4 ]
[ 21279-64-1 ]

Reference： [1]Agricultural and Biological Chemistry,1982,vol. 46,p. 2169 - 2172

9
[ 768-36-5 ]
[ 21279-64-1 ]

Reference： [1]Agricultural and Biological Chemistry,1982,vol. 46,p. 2169 - 2172

10
[ 21279-64-1 ]
5-Sulfopyrazine-2-carboxylic acid [ No CAS ]

Reference： [1]Agricultural and Biological Chemistry,1982,vol. 46,p. 2169 - 2172

11
[ 40255-48-9 ]
[ 110-17-8 ]
[ 21279-64-1 ]
2-[[2-[4-(2-Methoxyphenyl)piperazin-1-yl]ethyl]amino]-pyrazine-5-carboxamide (E)-but-2-enedioate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; In methanol; dichloromethane; acetonitrile;	3.3 2 -[[2-[4-(2-Methoxyphenyl)piperazin-1-yl]ethyl]amino]pyrazine-5-carboxamide (E)-but-2-enedioate 5.7 g (0.0242 mol) of 2-[4-(2-methoxyphenyl)-piperazin-1-yl]ethanamine, 3.82 g (0. 0242 mol) of <strong>[21279-64-1]2-chloropyrazine-5-carboxamide</strong>, 200 ml of acetonitrile and 3.35 g (0.0242 mol) of sodium carbonate are introduced into a 500 ml round-bottomed flask equipped with a reflux condenser and placed under nitrogen. The mixture is heated at reflux for 22 h, is allowed to cool and the solvent is evaporated under reduced pressure. The residue is purified by chromatography on a column of silica gel, the eluent being a 100/0 to 85/15 dichloromethane/methanol mixture, and the solid obtained is recrystallized from ethyl acetate. 0.96 g (0.0027 mol) of base is obtained. The fumarate is prepared from 0.96 g of base in solution in 50 ml of methanol and from 0.31 g (0.0027 mol) of fumaric acid in solution in 50 ml of methanol. The mixture is concentrated under reduced pressure and the product crystallizes. 0.97 g of white solid is obtained. Melting point: 220-222 C.

Reference： [1]Patent: US5420130,1995,A

12
[ 110-17-8 ]
[ 21279-64-1 ]
[ 160749-86-0 ]
2-[[3-[4-(5-Chloro-2-methoxyphenyl)piperazin-1-yl]propyl]amino]pyrazine-5-carboxamide (E)-but-2-enedioate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N-methyl-acetamide; ethanol;	5.3. 2-[[3-[4-(5-Chloro-2-methoxyphenyl)piperazin-1-yl]propyl]amino]pyrazine-5-carboxamide (E)-but-2-enedioate (1:1) 13.67 g (0.04817 mol) of 3-[4-(5-chloro-2-methoxyphenyl)piperazin-1-yl]propanamine, 8.65 g (0.062 mol) of potassium carbonate and 7.59 g (0.04817 mol) of <strong>[21279-64-1]2-chloropyrazine-5-carboxamide</strong> in suspension in 200 ml of dimethylformamide are introduced into a 500 ml round-bottomed flask and the mixture is stirred at room temperature for 48 h. The solvent is evaporated under reduced pressure, the residue is purified by recrystallization from ethyl acetate and 12.6 g of base are obtained. The fumarate is prepared from 1.58 g (0.0039 mol) of base in 50 ml of ethanol and from 0.47 g (0.0039 mol) of fumaric acid in 50 ml of ethanol. The mixture is concentrated and the product recrystallized from a methanol/ethanol mixture. 1.08 g (0.00207 mol) of white solid are finally obtained. Melting point=219-223 C. (decomposition).

Reference： [1]Patent: US5420130,1995,A

13
[ 33332-25-1 ]
[ 21279-64-1 ]

Yield	Reaction Conditions	Operation in experiment
43%	With trimethylaluminum; ammonium chloride; In toluene; benzene; at 0 - 50℃;	Production Example 195- [2- (4-hydrazinocarbonylmethylphenyl) ethyl] pyrazine-2- carboxamide dihydrochloride step 1[0129] Ammonium chloride (558 mg, 10.4 iranol) was suspended in benzene (5 ml) and 2M-trimethylaluminum toluene solution (5.2 ml, 10.4 mmol) was added dropwise at 0C. After stirring for 1 hr, a solution of methyl 5-chloropyrazine-2-carboxylate (600 mg, 3.48 mmol) in benzene (5 ml) was added. The reaction mixture was heated to 50C, and stirred overnight. After cooling, the reaction mixture was poured into water, and neutralized with saturated aqueous sodium hydrogen carbonate solution. The mixture was extracted with ethyl acetate, and the organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane:methanol = 100:0 -> 98:2) to give 5-chloropyrazine-2-carboxamide (236 mg, yield 43%) as a white solid.
	With ammonia; In methanol; water; at 20℃;	Preparation 10 To a solution of methyl 5-chloropyrazine-2-carboxylate (500 mg) in MeOH (5 mL) was added 28% NH3 aqueous solution (5 mL), and the mixture was stirred at ambient temperature. The precipitated solid was collected by filtration and washed with diisopropyl ether to afford 5-chloropyrazine-2-carboxamide (303 mg) as a solid.

Reference： [1]Patent: WO2009/145360,2009,A1 .Location in patent: Page/Page column 71
[2]Patent: EP2123651,2009,A1 .Location in patent: Page/Page column 21

14
[ 21279-64-1 ]
[ 36070-75-4 ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 5344 - 5354

15
[ 146093-46-1 ]
[ 21279-64-1 ]
[ 1352012-75-9 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In dimethyl sulfoxide; at 100℃; for 5h;Inert atmosphere;	Example 14 (compound No. 234)2,2,2-Trifluoro-1 -(trifluoromethyl)ethyl 4-[2-(5-carbamoylpyrazin-2-ylamino)ethyl]piperidine- 1 -carboxylate14.1 . ie f-Butyl 4-[2-(5-carbamoylpyrazin-2-ylamino)ethyl]piperidine-1 -carboxylate; A mixture of 1.12 g (7.15 mmol) of 5-chloropyrazine-2-carboxamide, 1.95 g (8.58 mmol) of ie f-butyl 4-(2-aminoethyl)piperidine-1 -carboxylate and 1 .18 g (8.58 mmol) of potassium carbonate in 1 .4 ml of dimethyl sulphoxide is heated during 5 hours at 100C under an argon atmosphere and with stirring. After cooling to ambient temperature, 25 ml of ethyl acetate and 25 ml of water are added. The organic phase is separated by settling and washed 3 times with 25 ml of water and then 25 ml of a saturated aqueous sodium chloride solution. It is dried over sodium sulphate and evaporated to dryness. The residue is purified by chromatography on silica gel, elution being carried out with a 97:3, then 95:5 and 93:7 mixture of dichloromethane and methanol, in order to obtain 1 .99 g (5.69 mmol) of product in the form of a light-yellow paste.1H NMR (CDCI3, delta ppm, 200 MHz): 8.65 (s, 1 H), 8.10 (s, 1 H), 7.55 (m, 1 H), 5.75 (m, 1 H), 4.85 (m, 1 H), 4.15 (m, 2H), 3.45 (m, 2H), 2.75 (t, 2H), 1 .80-1 .60 (m, 5H), 1 .50 (s, 9H), 1 .35-1 .10 (m, 2H).

Reference： [1]Patent: WO2011/151808,2011,A1 .Location in patent: Page/Page column 40-41

16
[ 21279-64-1 ]
[ 1352012-47-5 ]

Reference： [1]Patent: WO2011/151808,2011,A1

17
[ 21279-64-1 ]
5-(2-(piperidin-4-yl)ethylamino)pyrazine-2-carboxamide dihydrochloride [ No CAS ]

Reference： [1]Patent: WO2011/151808,2011,A1

18
[ 21279-64-1 ]
[ 89323-09-1 ]

Yield	Reaction Conditions	Operation in experiment
49%	With ammonium hydroxide; In methanol; at 95℃; for 0.5h;Microwave irradiation;	General procedure: Comp. 1a and 2a were prepared using microwave reactor. Special thick-walled tubes intended for use in microwave reactor were filled with a mixture of corresponding starting comp. 1 or 2 (150 mg, 0.952 mmol), 25% aqueous ammonia (2 mL, in excess) and MeOH (2 mL). Tubes fitted with stirrer and closed with a special cap were inserted into the reactor. Reaction conditions for microwave-assisted synthesis were: output 200 W, temperature 95 C, reaction time 30 min using PowerMAX mode.