[ CAS No. 10344-42-0 ] {[proInfo.proName]}

Name: 10344-42-0|4-Bromo-3,6-dichloropyridazine|95%
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SKU: A119794
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Quality Control of [ 10344-42-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 10344-42-0 ]

SDS Specification

Alternatived Products of [ 10344-42-0 ]

Product Details of [ 10344-42-0 ]

CAS No. :	10344-42-0	MDL No. :	MFCD13193322
Formula :	C₄HBrCl₂N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XAXKZIUQIROVNV-UHFFFAOYSA-N
M.W :	227.87	Pubchem ID :	22030648
Synonyms :

Calculated chemistry of [ 10344-42-0 ]

Physicochemical Properties

Num. heavy atoms :	9
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 :	39.75
TPSA :	25.78 Å²

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) :	-5.94 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.97
Log Po/w (XLOGP3) :	2.46
Log Po/w (WLOGP) :	2.55
Log Po/w (MLOGP) :	2.0
Log Po/w (SILICOS-IT) :	3.03
Consensus Log Po/w :	2.4

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.3
Solubility :	0.115 mg/ml ; 0.000506 mol/l
Class :	Soluble
Log S (Ali) :	-2.65
Solubility :	0.516 mg/ml ; 0.00226 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.74
Solubility :	0.0411 mg/ml ; 0.00018 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.91

Safety of [ 10344-42-0 ]

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 [ 10344-42-0 ]

* 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 [ 10344-42-0 ]
Downstream synthetic route of [ 10344-42-0 ]

[ 10344-42-0 ] Synthesis Path-Upstream 1~6

1
[ 10344-42-0 ]
[ 823-58-5 ]

Yield	Reaction Conditions	Operation in experiment
53%	With ammonia In ethanol at 20℃; Autoclave	4-Bromo-3,6-dichloro-pyridazine (15.0 g, 65.8 mmol, prepared as described in WO 20081 16815) was dissolved in EtOH (73.1 mL) and introduced into an autoclave. At rt, gaseous NH3 (4.48 g, 263mmol) was introduced, and the reaction mixture was then stirred over night at reflux. The solution was concentrated in vacuo and the residue was triturated with EtOAc, the insoluble part was filtrated off, and the mother liquor evaporated to give the crude product. This was purified by Flash-Chromatography, eluting with cyclohexan /EtOAc 1/1 +2.5percent Et3N, to give the title compound as a pale brown solid (5.82g, 53percent). LCMS (method ZCQ13): Rt. 0.3min, 164/166/168 (M+H)

Reference： [1] Patent: WO2015/715, 2015, A1, . Location in patent: Page/Page column 123; 124

2
[ 15456-86-7 ]
[ 6082-66-2 ]
[ 10344-42-0 ]

Reference： [1] Patent: WO2007/115947, 2007, A1, . Location in patent: Page/Page column 30

3
[ 15456-86-7 ]
[ 6082-66-2 ]
[ 1003944-29-3 ]
[ 10344-42-0 ]

Reference： [1] Patent: WO2008/9700, 2008, A1, . Location in patent: Page/Page column 38-39

4
[ 15456-86-7 ]
[ 10344-42-0 ]

Reference： [1] Patent: US6579875, 2003, B1,
[2] Patent: US6303605, 2001, B1,
[3] Patent: US6255305, 2001, B1,
[4] Patent: US6291460, 2001, B1,
[5] Patent: US6699859, 2004, B1,
[6] Patent: US6319924, 2001, B1,
[7] Heterocyclic Communications, 2015, vol. 21, # 4, p. 215 - 218

5
[ 15456-86-7 ]
[ 6082-66-2 ]
[ 10344-42-0 ]

Reference： [1] Patent: WO2007/115947, 2007, A1, . Location in patent: Page/Page column 30

6
[ 15456-86-7 ]
[ 6082-66-2 ]
[ 1003944-29-3 ]
[ 10344-42-0 ]

Reference： [1] Patent: WO2008/9700, 2008, A1, . Location in patent: Page/Page column 38-39

[ 10344-42-0 ] Synthesis Path-Downstream 1~21

1
[ 107-10-8 ]
[ 10344-42-0 ]
[ 227953-28-8 ]

Reference： [1]Heterocycles,1999,vol. 51,p. 1035 - 1050

3
[ 15456-86-7 ]
[ 6082-66-2 ]
[ 10344-42-0 ]

Yield	Reaction Conditions	Operation in experiment
	With trichlorophosphate; for 3.5h;Heating / reflux;	The solid in two batches was treated with phosphorus oxychloride (2x200 ml) and heated to reflux for 3.5 h. The mixture was cooled, evaporated and azeotroped with toluene. The residue was partitioned between dichloromethane and saturated aqueous sodium bicarbonate solution and extracted with DCM twice more. The organic extracts were dried and evaporated. This residue was re-dissolved in dichloromethane, and chromatographed on silica gel (300 g) (DCM as eluent) to give a white solid (101.5 g, 87%). (LC/MS analysis showed ca. 20-30% impurity, isomers of bromo- dichloropyridazine).MS (+ve ion electrospray) m/z 184/185/186 (MH+), trichloropyridazineMS (+ve ion electrospray) m/z 228/229/231 (MH+), bromo-dichloropyridazine.

Reference： [1]Patent: WO2007/115947,2007,A1 .Location in patent: Page/Page column 30

4
[ 6082-66-2 ]
[ 10344-42-0 ]
[ 17284-80-9 ]

Yield	Reaction Conditions	Operation in experiment
83%		(b) 2-[(3,6-Dichloro-4-pyridazinyl)oxy]ethanol; A solution of ethylene glycol (55 ml) in tetrahydrofuran (200 ml) was treated at around O0C (ice bath cooling) with sodium hydride (60% dispersion in oil, 5.9 g) over 40 minutes. After the addition was complete, 3,4,6- trichloropyridazine (27 g) containing isomers of bromo-dichloropyridazine as <n="32"/>impurity was added portionwise and washed in with more dry THF (50ml) and the mixture was stirred at O0C for 1 hour and then at room temperature overnight. The mixture was concentrated (to 1/3 volume) then diluted with aqueous sodium bicarbonate solution and extracted with chloroform (5x) and ethyl acetate (3x). The combined organic extracts were washed with water, dried over sodium sulphate and evaporated and the solids filtered off and washed with CHCI3 (x3) and dried in a vacuum oven overnight at 400C affording a white solid (25.5 g, 83%), containing some bromo-derivative (10-15%). MS (+ve ion electrospray) m/z 209/211 (MH+). MS (+ve ion electrospray) m/z 255/7 (MH+), bromo-derivative.

Reference： [1]Patent: WO2007/115947,2007,A1 .Location in patent: Page/Page column 30-31

5
[ 15456-86-7 ]
[ 6082-66-2 ]
[ 1003944-29-3 ]
[ 10344-42-0 ]

Yield	Reaction Conditions	Operation in experiment
	With trichlorophosphate; for 3.5h;Heating / reflux;	The solid in two batches was treated with phosphorus oxychloride (2x200 ml) and heated to reflux for 3.5 hours. The mixture was cooled, evaporated and azeotroped with <n="40"/>toluene. The residue was partitioned between dichloromethane and saturated aqueous sodium bicarbonate solution and extracted with DCM twice more. The organic extracts were dried and evaporated. This residue was re-dissolved in dichloromethane, and chromatographed on silica gel (300 g) (DCM as eluent) to give a white solid (101.5 g, 87%).(LC/MS analysis showed ca 20-30% impurity, isomers of bromo-dichloropyridazine).MS (+ve ion electrospray) m/z 184/185/186 (MH+), trichloropyridazine.MS (+ve ion electrospray) m/z 228/229/231 (MH+), bromo-dichloropyridazine.

Reference： [1]Patent: WO2008/9700,2008,A1 .Location in patent: Page/Page column 38-39

6
[ 109-83-1 ]
[ 10344-42-0 ]
2-(N-(3,6-dichloropyridazin-4-yl)-N-methylamino)ethanol [ No CAS ]

Reference： [1]Patent: US6362336,2002,B1 .Location in patent: Example 83

7
[ 123-75-1 ]
[ 10344-42-0 ]
[ 21415-33-8 ]

Yield	Reaction Conditions	Operation in experiment
100%	With potassium carbonate; In water; N,N-dimethyl-formamide;	c 3,6-Dichloro-4-(pyrrolidin-1-yl)pyridazine To a slurry of <strong>[10344-42-0]4-bromo-3,6-dichloropyridazine</strong> (115 g, 0.51 mol) and potassium carbonate (209 g, 1.5 mol) in DMF (1) was added pyrrolidine (46 ml, 0.56 mol) at 0 C. with stirring. The mixture was allowed to warm to room temperature and then stirred under nitrogen overnight. Water (1.5) was added and the resultant slurry was filtered. The residue was washed thoroughly with water and diethyl ether, yielding the title compound (110 g, 100%) as a fine white powder. 1H NMR (250 MHz, CDCl3) delta2.03 (4H, m), 3.64 (4H, m), 6.46 (1H, s). MS (ES+) m/e 218 [MH]+, 220 [MR]+.
92%	With potassium carbonate; In N,N-dimethyl-formamide;	b 3,6-Dichloro-4-(pyrrolidin-1-yl)pyridazine Pyrrolidine (3.36 ml, 40 mmol) was added to a stirred solution/suspension of <strong>[10344-42-0]4-bromo-3,6-dichloropyridazine</strong> (8.3 g, 36 mmol) and potassium carbonate (13.8 g, 0.1 mol) in dry DMF (100 ml) at room temperature under nitrogen. The mixture was stirred at room temperature for 16 hours, then at 60 C. for 3 hours. The reaction was poured into water (250 ml). The aqueous was extracted with ethyl acetate (*3). The combined extracts were dried (MgSO4), filtered and evaporated. The residue was purified by chromatography on silica gel, eluding with 0.5% methanol/dichloromethane to afford the title pyridazine (7.2 g, 92%) as a colourless oil. 1H NMR (250 MHz, CDCl3) 2.00-2.05 (4H, m) 3.61-3.69 (4H, m), 6.46 (1H, s). MS (ES+) 218 [MH]+, 220 [MH]+.
92%	With potassium carbonate; In N,N-dimethyl-formamide;	c 3,6-Dichloro-4-(pyrrolidin-1-yl)pyridazine Pyrrolidine (3.36 ml, 40 mmol) was added to a stirred solution/suspension of <strong>[10344-42-0]4-bromo-3,6-dichloropyridazine</strong> (8.3 g, 36 mmol) and potassium carbonate (13.8 g, 0.1 mol) in dry DMF (100 ml) at room temperature under nitrogen. The mixture was stirred at room temperature for 16 hours, then at 60 C. for 3 hours. The reaction was poured into water (250 ml). The aqueous was extracted with ethyl acetate (*3). The combined extracts were dried (MgSO4), filtered and evaporated. The residue was purified by chromatography on silica gel, eluding with 0.5% methanol/dichloromethane to afford the title pyridazine (7.2 g, 92%) as a colourless oil. 1H NMR (250 MHz, CDCl3) 2.00-2.05 (4H, m), 3.61-3.69 (4H, m), 6.46 (1H, s). MS (ES+) 218 [MH]+, 220 [MH]+.

92%

With potassium carbonate; In N,N-dimethyl-formamide;

c 3,6-Dichloro-4-(pyrrolidin-1-yl)pyridazine Pyrrolidine (3.36 ml, 40 mmol) was added to a stirred solution/suspension of <strong>[10344-42-0]4-bromo-3,6-dichloropyridazine</strong> (8.3 g, 36 mmol) and potassium carbonate (13.8 g, 0.1 mol) in dry DMF (100 ml) at room temperature under nitrogen. The mixture was stirred at room temperature for 16 h, then at 60 C. for 3 h. The reaction was poured into water (250 ml). The aqueous was extracted with ethyl acetate (*3). The combined extracts were dried (MgSO4), filtered and evaporated. The residue was purified by chromatography on silica gel, eluding with 0.5% methanol/dichloromethane to afford the title pyridazine (7.2 g, 92%) as a colourless oil. 1H NMR (250 MHz, CDCl3) 2.00-2.05 (4H, m), 3.61-3.69 (4H, m), 6.46 (1H, s). MS (ES+) 218 [MH]+, 220 [MH]+.

Reference： [1]Patent: US6699859,2004,B1
[2]Patent: US6579875,2003,B1
[3]Patent: US6303605,2001,B1
[4]Patent: US6291460,2001,B1

8
[ 15456-86-7 ]
[ 10344-42-0 ]

Yield	Reaction Conditions	Operation in experiment
42%	In dichloromethane; trichlorophosphate;	a 4-Bromo-3,6-dichloropyridazine A solution of <strong>[15456-86-7]4-bromo-1,2-dihydropyridazine-3,6-dione</strong> (Example 18, Step a) (10 g, 52 mmol) in phosphorus oxychloride (100 ml) was stirred and a heated at 100 C. under nitrogen for 16 hours. Upon cooling the excess phosphorus oxychloride was removed in vacuo. The residue was azeotroped with toluene (2), then taken up in dichloromethane/water. The mixture was carefully basified with sodium hydrogen carbonate (solid). It was necessary to dilute the mixture further to get two clear layers. The two layers were separated and the aqueous was extracted with dichloromethane (3). The combined extracts were dried (Na2SO4), filtered and evaporated. The residue was purified by chromatography on silica gel, eluding with dichloromethane to afford the title pyridazine (5.0 g, 42%) as a colourless solid. 1H NMR (250 MHz, CDCl3) 7.68 (br s). MS (ES+) 230 [MH]+, 228 [MH]+.
42%	In dichloromethane; trichlorophosphate;	b 4-Bromo-3.6-dichloropyridazine A solution of <strong>[15456-86-7]4-bromo-1,2-dihydropyridazine-3,6-dione</strong> (10 g, 52 mmol) in phosphorus oxychloride (100 ml) was stirred and heated at 100 C. under nitrogen for 16 hours. Upon cooling the excess phosphorus oxychloride was removed in vacuo. The residue was azeotroped with toluene (2), then taken up in dichloromethane/water. The mixture was carefully basified with sodium hydrogen carbonate (solid). It was necessary to dilute the mixture further to get two clear layers. The two layers were separated and the aqueous was extracted with dichloromethane (3). The combined extracts were dried (Na2SO4), filtered and evaporated. The residue was purified by chromatography on silica gel, eluding with dichloromethane to afford the title pyridazine (5.0 g, 42%) as a colourless solid. 1 H NMR (250 MHz, CDCl3) 7.68 (br s). MS (ES+) 230 [MH]+, 228 [MH]+.
42%	In dichloromethane; trichlorophosphate;	b 4-Bromo-3,6-dichloropyridazine A solution of <strong>[15456-86-7]4-bromo-1,2-dihydropyridazine-3,6-dione</strong> (10 g, 52 mmol) in phosphorus oxychloride (100 ml) was stirred and heated at 100 C. under nitrogen for 16 hours. Upon cooling the excess phosphorus oxychloride was removed in vacuo. The residue was azeotroped with toluene (2), then taken up in dichloromethane/water. The mixture was carefully basified with sodium hydrogen carbonate (solid). It was necessary to further dilute the mixture to get two clear layers. The two layers were separated and the aqueous was extracted with dichloromethane (3). The combined extracts were dried (Na2SO4), filtered and evaporated. The residue was purified by chromatography on silica gel, eluding with dichloromethane to afford the title compound (5.0 g, 42%) as a colourless solid. 1H NMR (250 MHz, CDCl3) delta 7.68 (1H, br s). MS (ES+) m/e 230 [MH]+, 228 [MH]+.

42%	In dichloromethane; trichlorophosphate;	b 4-Bromo-3,6-dichloropyridazine A solution of <strong>[15456-86-7]4-bromo-1,2-dihydropyridazine-3,6-dione</strong> (10 g, 52 mmol) in phosphorus oxychloride (100 ml) was stirred and heated at 100 C. under nitrogen for 16 h. Upon cooling the excess phosphorus oxychloride was removed in vacuo. The residue was azeotroped with toluene (2), then taken up in dichloromethane/water. The mixture was carefully basified with sodium hydrogen carbonate (solid). It was necessary to dilute the mixture further to get two clear layers. The two layers were separated and the aqueous was extracted with dichloromethane (3). The combined extracts were dried (Na2SO4), filtered and evaporated. The residue was purified by chromatography on silica gel, eluding with dichloromethane to afford the title pyridazine (5.0 g, 42%) as a colourless solid. 1H NMR (250 MHz, CDCl3) 7.68 (br s). MS (ES30) 230 [MH]+, 228 [MH]+.
42%	In dichloromethane; trichlorophosphate;	b 4-Bromo-3,6-dichloropyridazine A solution of <strong>[15456-86-7]4-bromo-1,2-dihydropyridazine-3,6-dione</strong> (10 g, 52 mmol) in phosphorus oxychloride (100 ml) was stirred and heated at 100 C. under nitrogen for 16 hours. Upon cooling the excess phosphorus oxychloride was removed in vacuo. The residue was azeotroped with toluene (2), then taken up in dichloromethane/water. The mixture was carefully basified with sodium hydrogen carbonate (solid). It was necessary to dilute the mixture further to get two clear layers. The two layers were separated and the aqueous was extracted with dichloromethane (3). The combined extracts were dried (Na2SO4), filtered and evaporated. The residue was purified by chromatography on silica gel, eluding with dichloromethane to afford the title compound (5.0 g, 42%) as a colourless solid. 1H NMR (250 MHz, CDCl3) delta7.68 (1H, br s). MS (ES+) m/e 230 [MH]+, 228 [MH]+.
	In dichloromethane; trichlorophosphate;	b) 4-Bromo-3,6-dichloropyridazine A solution of <strong>[15456-86-7]4-bromo-1,2-dihydropyridazine-3,6-dione</strong> (10 g, 52 mmol) in phosphorus oxychloride (100 ml) was stirred and heated at 100 C. under nitrogen for 16 hours. Upon cooling the excess phosphorus oxychloride was removed in vacuo. The residue was azeotroped with toluene (2), then taken up in dichloromethane/water, The mixture was carefully basified with sodium hydrogen carbonate (solid). It was necessary to dilute the mixture further two get two clear layers. The two layers were separated and the aqueous was extracted with dichloromethane (3). The combined extracts were dried (Na2SO4), filtered and evaporated. The residue was purified by chromatography on silica gel, eluding with dichloromethane to afford the title pyridaziyze (5.0 g, 42%) as a colourless solid. 1H NMR (250 MHz, CDCl3) 7.68 (br s). MS (ES+) 230 [MH]+, 228 [MH]+.

Reference： [1]Patent: US6579875,2003,B1
[2]Patent: US6303605,2001,B1
[3]Patent: US6255305,2001,B1
[4]Patent: US6291460,2001,B1
[5]Patent: US6699859,2004,B1
[6]Patent: US6319924,2001,B1
[7]Heterocyclic Communications,2015,vol. 21,p. 215 - 218

9
[ 694-05-3 ]
[ 10344-42-0 ]
3,6-dichloro-4-(3,6-dihydro-2H-pyridin-1-yl)pyridazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	With potassium carbonate; In N,N-dimethyl-formamide;	c) 3,6-Dichloro-4-(3,6-dihydro-2H-pyridin-1-yl)pyridazine 1,2,3,6-Tetrahydropyridine, (1.04 ml) was added to a stirred solution/suspension of <strong>[10344-42-0]4-bromo-3,6-dichloropyridazine</strong> (2.0 g, 8.8 mmol) and potassium carbonate (2.4 g) in dry DMF (10 ml) at room temperature under nitrogen. The mixture was stirred at room temperature for 5 hours. The reaction was poured into water (100 ml) and extracted with ethyl acetate (*3). The combined extracts were washed with water (200 ml), brine, dried (MgSO4), filtered and evaporated. The residue was triturated with ether/petroleum ether to afford a white powder (1.96 g, 97%). 1H NMR (250 MHz, CDCl3) 6.82 (1H, s), 5.97 (1H, m), 5.80 (1H, m), 3.77 (2H, m), 3.59 (2H, m), 2.38 (2H, m). MS (ES+) 232 [MH]+.

Reference： [1]Patent: US6319924,2001,B1

10
[ 10344-42-0 ]
2-(N-(3,6-dichloropyridazin-4-yl)-N-methylamino)ethanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	In isopropyl alcohol;	The starting material was prepared as follows: A solution of <strong>[10344-42-0]4-bromo-3,6-dichloro-pyridazine</strong> (1.11 g, 5 mmol). (J. Chem. Soc., Perkin Trans I, 1974, 696), and 2-(methylamino)ethanol (0. 75 g, 10 mmol) in isopropanol (10 ml) was heated at reflux for 30 minutes. The solvent was removed by evaporation, the residue was partitioned between methylene chloride and water and the aqueous layer was adjusted to pH9 with solid potassium carbonate. The organic layer was separated, washed with brine, dried (MgSO4) and the solvent removed by evaporation. The residue was triturated with ether, collected by filtration and dried under vacuum to give 2-(N-(3,6-dichloropyridazin-4-yl)-N-methylamino)ethanol (1 g, 90%). 1 H NMR Spectrum: (CDCl3) 2.1(br s, 1H); 3.09(s, 3H); 3.71(t, 2H); 3.93(t, 2H); 6.8(s, 1H) MS-ESI: 221 [MH]+

Reference： [1]Patent: US5962458,1999,A

11
[ 10344-42-0 ]
[ 60-34-4 ]
[ 1063698-57-6 ]

Reference： [1]Journal of Heterocyclic Chemistry,2011,vol. 48,p. 149 - 152
[2]Heterocyclic Communications,2012,vol. 18,p. 39 - 42

12
[ 10344-42-0 ]
[ 823-58-5 ]

Yield	Reaction Conditions	Operation in experiment
53%	With ammonia; In ethanol; at 20℃;Autoclave;	4-Bromo-3,6-dichloro-pyridazine (15.0 g, 65.8 mmol, prepared as described in WO 20081 16815) was dissolved in EtOH (73.1 mL) and introduced into an autoclave. At rt, gaseous NH3 (4.48 g, 263mmol) was introduced, and the reaction mixture was then stirred over night at reflux. The solution was concentrated in vacuo and the residue was triturated with EtOAc, the insoluble part was filtrated off, and the mother liquor evaporated to give the crude product. This was purified by Flash-Chromatography, eluting with cyclohexan /EtOAc 1/1 +2.5% Et3N, to give the title compound as a pale brown solid (5.82g, 53%). LCMS (method ZCQ13): Rt. 0.3min, 164/166/168 (M+H)

Reference： [1]Patent: WO2015/715,2015,A1 .Location in patent: Page/Page column 123; 124

13
[ 10344-42-0 ]
[ 137-07-5 ]
[ 10344-41-9 ]