[ CAS No. 4774-14-5 ] {[proInfo.proName]}

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2D 3D

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Quality Control of [ 4774-14-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 4774-14-5 ]

SDS Specification

Alternatived Products of [ 4774-14-5 ]

Product Details of [ 4774-14-5 ]

CAS No. :	4774-14-5	MDL No. :	MFCD00006125
Formula :	C₄H₂Cl₂N₂	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	LSEAAPGIZCDEEH-UHFFFAOYSA-N
M.W :	148.98	Pubchem ID :	78504
Synonyms :

Calculated chemistry of [ 4774-14-5 ] Expand+

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	32.05
TPSA :	25.78 ?2

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) :	-6.12 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.51
Log Po/w (XLOGP3) :	1.53
Log Po/w (WLOGP) :	1.78
Log Po/w (MLOGP) :	0.4
Log Po/w (SILICOS-IT) :	2.34
Consensus Log Po/w :	1.51

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.28
Solubility :	0.777 mg/ml ; 0.00522 mol/l
Class :	Soluble
Log S (Ali) :	-1.68
Solubility :	3.11 mg/ml ; 0.0209 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.87
Solubility :	0.203 mg/ml ; 0.00136 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.05

Safety of [ 4774-14-5 ]

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

Application In Synthesis of [ 4774-14-5 ]

* 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 [ 4774-14-5 ]
Downstream synthetic route of [ 4774-14-5 ]

[ 4774-14-5 ] Synthesis Path-Upstream 1~1

1
[ 4774-14-5 ]
[ 77287-34-4 ]
[ 312736-50-8 ]

Yield	Reaction Conditions	Operation in experiment
36%	at 20 - 90℃; for 14 h;	To a mixture of 2,6-dichloropyrazine (11.0 g, 73.8 mmol) and formamide (58.6 mL, 1,476 mmol) was added dropwise sodium persulfate (17.1 g, 71.7 mmol). The reaction mixture was stirred at 90 for 2 h and was further stirred at rt for 12 h. After dilution with water, the mixture was extracted with isopropanol/chloroform (1/3) and washed with brine. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography (70percent n-hexane/EtOAc) to afford 3,5-dichloropyrazin-2-carboxamide (5.06 g, 36percent) as an oil.
36%	at 90℃;	107241 2,6-Dichloropyrazine (55 g, 0.37 mol) and formamide (300 mL) were combined and heatedto 90 °C. Sodium persulfate (86.7 g, 0.36 mol) was added to the mixture at 90 °C in portions (1 g)20-3 0 second intervals. An exotherm was observed and the color of the mixture turned from yellowto dark red/brown. The mixture was stirred at 90 °C for 2 h and then cooled to room temperature.The mixture was diluted with water (500 mL) and filtered. The filtrate layers were separated. Theaqueous layer was extracted with IPAchloroform (1/3, 3 x 750 mL). The combined organic layers were dried over sodium sulfate and concentrated under vacuum to afford a viscous oil. The oil was purified by silica gel chromatography (0 to 100percent EtOAc in hexanes) to provide the title product as a colorless solid (25 g, 36percent yield). ‘HNMR (400 IVIHz, DMSO-d6): ppm 8.87 (s, 1H), 8.18 (br. s.,1H), 8.01 (br. s., 1H).
36%	at 90℃; for 2 h;	2,6-Dichloropyrazine (55 g, 0.37 mol) and formamide (300 mL) were combined and heated to 90° C. Sodium persulfate (86.7 g, 0.36 mol) was added to the mixture at 90° C. in Ig portions at 20-30 seconds intervals. An exotherm was observed and the color of the mixture turned from yellow to dark red/brown. The mixture was stirred at 90° C. for 2 h and then cooled to room temperature. The mixture was diluted with water (500 mL) and filtered. The filtrate layers were separated. The aqueous layer was extracted with IPA:chloroform (1:3, 3*750 mL). The combined organic layers were dried over sodium sulfate and concentrated under vacuum to afford a viscous oil. The oil was purified by silica gel chromatography (0 to 100percent ethyl acetate in hexanes) to provide the title product as a colorless solid (25 g, 36percent yield).

Reference： [1] Organic Letters, 2013, vol. 15, # 9, p. 2156 - 2159
[2] Patent: WO2016/6975, 2016, A2, . Location in patent: Paragraph 457-459
[3] Patent: KR2016/7347, 2016, A, . Location in patent: Paragraph 0359; 0360; 0361; 0362
[4] Patent: WO2018/22992, 2018, A1, . Location in patent: Paragraph 0723; 0724
[5] Patent: US2018/72743, 2018, A1, . Location in patent: Paragraph 1328-1329

[ 4774-14-5 ] Synthesis Path-Downstream 1~10

1
[ 4774-14-5 ]
[ 33332-28-4 ]

Yield	Reaction Conditions	Operation in experiment
95%	With ammonia; at 100℃; for 5h;	In the hydrothermal reaction kettle are respectively added with 2, 6 - two chlorine pyrrole qin (10.0 g, 67.1 mmol) and ammonia (100 ml), 100 C lower reaction 5 h. The completion of the reaction, cooling to room temperature, filtered, the filter cake is hexane (16 ml) beating shall 2 - amino -6 - chloropyrazine white solid 8.2 g, yield is 95.0%.
91%	With ammonia; In water; at 100℃; for 18h;Sealed tube;	2,6-Dichloropyrazine (2.89 g, 19.4 mmol) was stirred in aqueous NH3 (28%, 10 ml.) and heated to 100C in a sealed tube for 18 hours. The reaction mixture was cooled and the resultant precipitate was filtered. Trituration with water and then ether gave 6- chloropyrazin-2-amine as a white solid (2.28 g, 17.6 mmol, 91 % yield). 1H NMR (d6-DMSO, 400 MHz) ? 6.9 (brs, 2H), 7.70 (d, J = 0.4, 1 H), 7.80 (d, J = 0.4, 1 H); LC-MS (ZQ, 6 minutes) Rt = 1.05 minutes; m/z (ESI+) 130 (M+H).6-Chloropyrazin-2-amine (2.50 g, 19.3 mmol) was stirred in CH2CI2 (60 ml.) at 0C.A/-Bromosuccinimide (2.92 g, 16.4 mmol) was added slowly and the reaction mixture was stirred at 0C for 60 minutes. The reaction mixture was filtered through celite and concentrated to give a brown oil. Purification by flash chromatography, eluting with 0-25% EtOAc-hexanes, gave 5-bromo-6-chloropyrazin-2-amine as a yellow solid (1 .69 g, 8.16 mmol, 42% yield). 1H NMR (de-DMSO, 400 MHz) ? 7.1 (brs, 2H), 7.65 (s, 1 H); LC-MS (ZQ, 4 minutes) Rt = 1.46 minutes; m/z (ESI-) 205 (M-H).A mixture of 5-bromo-6-chloropyrazin-2-amine (1 .00 g, 4.8 mmol), copper (I) iodide (914 mg, 4.8 mmol), 18-crown-6 (95 mg, 0.36 mmol) andtetrakis(triphenylphosphine)palladium (0) (83 mg, 0.072 mmol) was suspended in dry DMF (20 ml.) and a stream of nitrogen was passed through for 5 minutes. Potassium cyanide (312 mg, 4.8 mmol) was added and the mixture was stirred at room temperature for 30 minutes, then refluxed at 200C for 3 hours. The mixture was cooled, diluted with EtOAc and absorbed onto silica gel (10 g). DMF was removed by evaporation. The product was purified by flash chromatography, eluting with 1 :1 EtOAc-hexanes, to yield 5- amino-3-chloropyrazine-2-carbonitrile as a yellow solid (607 mg, 3.93 mmol, 82% yield). 1H NMR (d6 DMSO, 400 MHz) ? 7.87 (s, 1 H), 8.1 (brs, 2H); LC-MS (ZQ, 4 minutes) Rt = 1.20 minutes; m/z (ESI-) 153 (M-H).
80%	With ammonia; In water; at 135℃;Autoclave;	A solution of compound 8 4500 g, 302 mol) in conc. aq. NH3 (3.0 L) was stirred at135C overnight in a 10 L sealed pressure vessel. TLC and LC/MS showed completeconversion of the starting material. The reaction mixture was cooled to roomtemperature and filtered to afford a white solid. The solid was washed with water (200mL x 3), and then dried to afford compound 9 (312 g, 80% yield) as a solid.1HNMR (400 MHz, DMSO-d6): 7,82 (s, 1 H), 712 (s, 1 H), 6.93 (s, 2H). MS Calcd.:129 MS Found: 130 ([M+Hj).

80%	With ammonium hydroxide; at 135℃;Sealed tube;	A solution of compound 8 (450.0 g, 3.02 mol) in cone. aq. NH3 (3.0 L) was stirred at 135°C overnight in a 10 L sealed pressure vessel. TLC and LC/MS showed complete conversion of the starting material. The reaction mixture was cooled to room temperature and filtered to afford a white solid. The solid was washed with water (200 mL x 3), and then dried to afford compound 9 (312 g, 80percent yield) as a solid. 1HNMR (400 MHz, DMSO- 6): delta 7.82 (s, 1 H), 7.12 (s, 1 H), 6.93 (s, 2H). MS Calcd.: 129 MS Found: 130 ([M+H]+).
63%	With ammonia; In water; at 20 - 140℃; for 63h;In sealed autoclave;	EXAMPLE 5 2-amino-6-chloropyrazine 120 ml of water, 20.8 ml (0.31 mol, 4.6 eq) of an aqueous 28% ammonia solution and 10 g (0.067 mol, 1 eq) of 2,6-dichloropyrazine were successively added to an autoclave reactor. The autoclave was sealed and the mixture heated at 140 C. for 3 h, then left at room temperature for 60 h. The mixture was filtered, the precipitate washed with water, then vacuum dried. The reaction produced 5.4 g of a fine powder (yield: 63%). 1H NMR (CDCl3) delta (ppm): 7.88 (s, 1H, CH); 7.84 (s, 1H, CH); 4.68 (m, 2H, NH2). HPLC: t=1.07 min MS: 130 (MH+) HPLC purity: 100%
60%	With ammonium hydroxide; In water; at 120℃; for 6h;Large scale;	A solution of 2,6-dichloropyrazine (15kg, 1O1.4mol, 1.00 equiv) in water(20 L), ammonia water (25 L, 25 %) was placed in a 100 L pressure tank reactor. The resulting solution was stirred for 6 h at 120C. The reaction progress was monitored by TLC (EA:PE = 1 : 1) until the starting material was consumed, and cooled to room temperature. Thesolids were collected by filtration. The solid was washed with water and dried. The solidwas washed with petroleum ether to remove the unreacted starting materials. The product (7.8kg, purity = 95 %, 60% yield) was obtained as a white solid.
59.7%	With ammonia; In water; at 140℃; for 14h;	Example B-10: Preparation of (2S)-1-(4-(1-isopropyl-3-(5-methyl-5H-pyrrolo[3,2-b]pyrazin-2-yl)-1H- pyrazol-4-yl)pyrimidin-2-ylamino)propan-2-ol (B-10) <n="80"/>cr Et3NB-10-1 B-10-2 B-10-3Preparation of 6-chloropyrazin-2-amine (B-10-2). B-10-1 B-10-2A mixture of 2,6-dichloropyrazine (300 g, 2 mol) and 28% aq. NH3 (8 L) was stirred at 14O0C in a sealed system for 14 hours. TLC (petroleum ether/EtOAc 3:1 ) indicated complete consumption of starting material. The reaction mixture was extracted with EtOAc (3 L x 3). The combined organic layers were washed with saturated aqueous NaCI (3 L), dried over Na2SO4 and concentrated in vacuo to give crude compound B-10-2, which was purified by column chromatography (silica gel, petroleum ether/EtOAc 2:1) to yield pure compound B-10-2 (410 g, yield: 59.7%) as a white solid.
41.98 g (48%)	In ammonia;	3. 2-Chloro-6-amino-pyrazine A suspension of 2,6-dichloropyrazine (100 g, 0.67 mole, Lancaster) in 0.880 ammonia (500 ml) was stirred and heated at 150 C. in a glass lined autoclave at 20 atm for 16 hrs. The cooled mixture was filtered, washed well with water (200 ml) and dried. The product was recrystallized from chloroform. Yield 41.98 g (48%), M.p. 150-152 C.
	With ammonia; In water; at 100℃;Autoclave;	Svnthesis 2-1-A 6-Chloropyrazin-2-amine 2,6-Dichloropyrazine (2.89 g, 19.4 mmol) was stirred in aqueous ammonia (28%, 10 mL) and heated to 100C overnight in a sealed tube. The reaction mixture was cooled and the resultant precipitate was filtered. Trituration with water and then ether gave the title compound as a white solid (2.28 g, 17.6 mmol, 91%). 1H NMR (d6-DMSO, 400 MHz) delta 7.80 (d, 1 H1 J = 0.4 Hz), 7.70 (d, 1 H, J = 0.4 Hz), 6.9 (br s, 2H). LC-MS (2) rt 1.05 min; m/z (ESI+) 130/132.

Reference： [1]Patent: CN107857737,2018,A .Location in patent: Paragraph 0011-0013; 0021-0023; 0030-0032; 0040-0042; 0049
[2]Journal of Medicinal Chemistry,2011,vol. 54,p. 8328 - 8342
[3]Patent: WO2013/68755,2013,A1 .Location in patent: Page/Page column 67, 68
[4]Patent: WO2017/5786,2017,A1 .Location in patent: Page/Page column 23; 24
[5]Patent: WO2018/9424,2018,A1 .Location in patent: Paragraph 00195; 00198-00199
[6]Tetrahedron,1984,vol. 40,p. 5081 - 5088
[7]Patent: US2005/267126,2005,A1 .Location in patent: Page/Page column 10-11
[8]Patent: WO2017/29602,2017,A2 .Location in patent: Paragraph 75; 133; 134
[9]Patent: WO2009/16460,2009,A2 .Location in patent: Page/Page column 78-79
[10]Patent: US6255307,2001,B1
[11]Patent: WO2009/103966,2009,A1 .Location in patent: Page/Page column 88

2
[ 6863-76-9 ]
[ 19745-07-4 ]
[ 4858-85-9 ]
[ 4774-14-5 ]

Reference： [1]Journal of Heterocyclic Chemistry,1994,vol. 31,p. 1177 - 1180
[2]Journal of Heterocyclic Chemistry,1994,vol. 31,p. 1177 - 1180

3
[ 6863-76-9 ]
[ 14508-49-7 ]
[ 19745-07-4 ]
[ 4858-85-9 ]
[ 4774-14-5 ]

Reference： [1]Journal of Chemical Research, Miniprint,1984,p. 2860 - 2875

4
[ 290-37-9 ]
[ 7732-18-5 ]
[ 7782-50-5 ]
[ 14508-49-7 ]
[ 19745-07-4 ]
[ 4858-85-9 ]
[ 4774-14-5 ]

Reference： [1]Patent: US2540476,1948,

5
[ 17413-10-4 ]
[ 4774-14-5 ]
2-(2,3-dihydro-1,4-benzodioxin-6-methylamino)-6-chloropyrazine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 407 - 416

6
[ 4774-14-5 ]
[ 442850-71-7 ]
[ 1010086-61-9 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate;tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 100℃;	(1) Synthesis of N-(1-tert-butyl-1H-pyrazol-5-yl)-6-chloropyrazin-2-amineA mixture of 60.6 g of 2,6-dichloropyrazine, 62.2 g of <strong>[442850-71-7]1-tert-butyl-1H-pyrazol-5-amine</strong> as obtained in Reference 3, 23.5 g of 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene, 21.0 g of tris(dibenzylideneacetone)dipalladium(0)-chloroform complex, 172.6 g of potassium phosphate and 1.17 l of 1,4-dioxane was stirred at 100 C. overnight, followed by cooling down to room temperature. An insoluble matter was filtered off using Celite and washed with ethyl acetate. The resulting ethyl acetate solution was washed with water and brine, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated in vacuo. The obtained residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate=4/1-2/1) to give the title compound as a yellow solid.

Reference： [1]Patent: US2008/58347,2008,A1 .Location in patent: Page/Page column 42

7
[ 1123-93-9 ]
[ 4774-14-5 ]
[ 1175018-53-7 ]

Yield	Reaction Conditions	Operation in experiment
53%	With sodium t-butanolate;palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 85℃; for 16h;Product distribution / selectivity;	A mixture of 2,6-dichloropyrazine (0.150 g, 1.006 mmol), 5-amino-benzothiazole (0.151 g , 1.006 mmol), BINAP (0.0137 g, 0.02215 mmol), sodium tertiary butoxide (0.136 g, 1.409 mmol) and palladium acetate (0.005 g, 0.02215 mmol) in toluene (8 mL) was heated at 85 0C for 16 h under nitrogen. CH2CI2 was added, the reaction mixture was filtered through Celite, and the solvent was evaporated. The residue was purified by column chromatography (5percent methanol in CH2CI2 as eluent) to give 0.140 g (53percent) of intermediate benzothiazol-5-yl-(6-chloro-pyrazin-2-yl)-amine. 1H NMR (CDCl3) delta 10.12 (s, IH), 9.38 (s, IH), 8.59 (s, IH), 8.22 (s, IH), 8.11-8.08 (d, J= 8.67 Hz, 1 H), 8.02 (s, IH), 7.6-7.57 (d, J= 8.67 Hz, 1 H); MS (API-E S/Positive); m/z: 263 (M+H)+.

Reference： [1]Patent: WO2009/95399,2009,A2 .Location in patent: Page/Page column 36

8
[ 56525-79-2 ]
[ 4774-14-5 ]
C₅₂H₃₄N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1.8 g	With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; tri tert-butylphosphoniumtetrafluoroborate; In toluene; for 8h;Inert atmosphere; Reflux;	In the argon atmosphere, 2,6-dichloropyrazine (0.6 g, 3.9 mmol) was added sequentially, 3,6-dibromocarbazole (2.6 g, 8 mmol), (Dibenzylideneacetone) dipalladium (0.07 g, 0.08 mmol) Tri-t-butylphosphonium tetrafluoroborate (0.09 g, 0.3 mmol) (0.5 g, 5.5 mmol) and anhydrous toluene (20 mL), And heated to reflux for 8 hours. After the reaction solution was allowed to cool to room temperature, Separating the organic layer, The organic solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography, A solid of 1.8 g was obtained. For the resulting compound, As a result of FD-MS, Identified as compound BH-1.
1.8 g	With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; tri tert-butylphosphoniumtetrafluoroborate; In toluene; for 8h;Inert atmosphere; Reflux;	In the argon atmosphere,Add it in sequence2,6-dichloropiperidine(0.6 g, 3.9 mmol),3,6-dibromocarbazole (2.6 g, 8 mmol),(Dibenzylideneacetone) dipalladium (0.07 g, 0.08 mmol)Tri-butyl-tetrafluoroborate (0.09 g, 0.3 mmol)(0.5 g, 5.5 mmol) and anhydrous toluene (20 mL),And heated to reflux for 8 hours.After the reaction solution was allowed to cool to room temperature,Separating the organic layer,The organic solvent was distilled off under reduced pressure.The resulting residue was purified by silica gel column chromatography,A solid of 1.8 g was obtained.

Reference： [1]Patent: TWI554499,2016,B .Location in patent: Page/Page column 89; 90
[2]Patent: TW2016/38086,2016,A .Location in patent: Page/Page column 41; 42; 43

9
[ 13726-16-4 ]
[ 4774-14-5 ]
(4-chloro-3-methoxyphenyl)(3,5-dichloropyrazin-2-yl)methanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
17%		(4-Chloro-3-methoxyphenyl)(3,5-dichloropyrazin-2-yl)methanol To a -78° C. solution of LDA (2.0M in hexane, 22.0 mmol) in dry THF (40 mL), under argon was added a solution of 2,6-dichloropyrazine (1.648 g, 11.0 mmol) in THF (10 mL). After addition was completed, the resulting mixture was stirred at -78° C. for an additional 1 h, then <strong>[13726-16-4]4-chloro-3-methoxybenzaldehyde</strong> (2.81 g, 16.5 mmol) in THF (10 mL) was added dropwise. The reaction mixture was stirred for another hour, then quenched with hydrochloric acid (1.8 mL)/EtOH (7.5 mL)/THF (9.0 mL) mixture, and warmed to RT. The reaction mixture was diluted with saturated aqueous sodium bicarbonate solution and extracted with EtOAc. The organic layer was separated and washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (petroleum ether:EtOAc=4:1) to give the title compound (600 mg, 17percent). MS (ES+) C12H9Cl3N2O2 requires: 318, found: 319 [M+H]+.

Reference： [1]Patent: US2017/342078,2017,A1 .Location in patent: Paragraph 0515; 0516

10
[ 4774-14-5 ]
[ 133773-29-2 ]
(R)-6-chloro-N-(1-(2,4-dichlorophenyl)ethyl)pyrazin-2-amine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2019,vol. 62,p. 6190 - 6213

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[ 4774-14-5 ]

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