[ CAS No. 923595-49-7 ] {[proInfo.proName]}

Name: 923595-49-7|6-Chloro-3-iodoimidazo[1,2-b]pyridazine|96%
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SKU: A132051
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Quality Control of [ 923595-49-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 923595-49-7 ]

Product Details of [ 923595-49-7 ]

CAS No. :	923595-49-7	MDL No. :	MFCD11044749
Formula :	C₆H₃ClIN₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	IWHCPHZAMFSDFM-UHFFFAOYSA-N
M.W :	279.47	Pubchem ID :	53249897
Synonyms :

Calculated chemistry of [ 923595-49-7 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	50.71
TPSA :	30.19 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) :	-6.61 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.91
Log Po/w (XLOGP3) :	1.97
Log Po/w (WLOGP) :	1.99
Log Po/w (MLOGP) :	2.1
Log Po/w (SILICOS-IT) :	2.09
Consensus Log Po/w :	2.01

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.42
Solubility :	0.106 mg/ml ; 0.000381 mol/l
Class :	Soluble
Log S (Ali) :	-2.23
Solubility :	1.65 mg/ml ; 0.0059 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.28
Solubility :	0.148 mg/ml ; 0.000528 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.45

Safety of [ 923595-49-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280	UN#:	N/A
Hazard Statements:	H317	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 923595-49-7 ]

* 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 [ 923595-49-7 ]
Downstream synthetic route of [ 923595-49-7 ]

[ 923595-49-7 ] Synthesis Path-Upstream 1~1

1
[ 6775-78-6 ]
[ 923595-49-7 ]

Yield	Reaction Conditions	Operation in experiment
90%	With N-iodo-succinimide In chloroform at 20℃;	Preparation of 6-chloro-3-iodoimidazo[1,2-b]pyridazine 6-chloroimidazo[1,2-b]pyridazine (2.0 g, 13.0 mmol, 1.0 equiv) in chloroform (20 mL) at room temperature was added N-iodosuccinimide (2.9 g, 13.0 mmol, 1.0 equiv) then stirred vigorously overnight. The reaction mixture was diluted in water and extracted with ethyl acetate. Purification using column chromatography gave 3.3 g of the yellow solid, 90percent: 1H NMR δ 8.21 (d, J=7.6 Hz, 1H), 7.96 (s, 1H), 7.41 (d, J=7.6 Hz, 1H).
75%	With iodine In dimethyl sulfoxide at 20℃; for 36 h;	Example 15 -3 Synthesis of 6-chloro-3-iodo-imidazo[1,2-b]pyridazine 6-chloroimidazo[1,2-b]pyridazine 1a (28.0 g, 0.182 mol) was dissolved in DMSO (196 ml). Iodine (55.0 g, 0.219 mol) was then added and the reaction mixture was stirred at room temperature for 36 hours. The mixture was poured onto a saturated aqueous sodium bicarbonate solution (250 ml) and extracted with dichloromethane (2 x 250ml). The organic layer was washed with an aqueous solution of sodium meta bisulfite (250 ml) followed by brine (250 ml). It was then dried (Na₂SO₄) and evaporated under reduced pressure. The residue was recrystallised from ethyl acetate to give 23 g (75 percent) of 6-chloro-3-iodo-imidazo[1,2-b]pyridazine 5 as an off white solid. ¹H-NMR (400 MHz, DMSO-d₆) : δ = 8.27 (1 H, d, J = 9.5 Hz), 8.02 (1 H, s), 7.46 (1 H, d, J = 9.5 Hz). LCMS-ESI (m/z); found 280.0 [M+H]⁺.
1.4 g	With N-iodo-succinimide In acetonitrile at 60℃; for 10 h;	Synthesis of 6-chloro-3-iodoimidazo[l , 2-bJpyridazine To a degassed solution of 6-chloroimidazo[l,2-b]pyridazine (1.0 g, 6.51 mmol) and NIS (2.2 g, 9.77 mmol) in MeCN (30 mL) was heated to 60 °C for 10 hours. The reaction mixture was cooled to RT and extract with DCM. The organics were washed with Na₂S₂0₃ (aq), brine and dried over Na₂S0₄. After concentrated, the crude product was purified by column (PE : EA = 5 : 1) to obtain 6-chloro-3-iodoimidazo[l,2-b]pyridazine (1.4 g, yield: 83percent). 1H- MR (CDC1₃, 400 MHz) δ 7.83 (s, 1H), 7.80 (d, J= 4.8 Hz, 1H), 7.04 (d, J= 9.6 Hz, 1H). MS(M+H)⁺: 280.

Reference： [1] Patent: US2014/256733, 2014, A1, . Location in patent: Page/Page column 0227; 0230-0231
[2] MedChemComm, 2018, vol. 9, # 10, p. 1733 - 1745
[3] Patent: EP2818471, 2014, A1, . Location in patent: Paragraph 0120; 0121
[4] Patent: WO2013/34048, 2013, A1, . Location in patent: Page/Page column 77; 78
[5] Journal of Medicinal Chemistry, 2014, vol. 57, # 6, p. 2789 - 2798
[6] Journal of the American Chemical Society, 2015, vol. 137, # 2, p. 592 - 595

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24%	With N-iodo-succinimide; In acetonitrile; at 20℃; for 14h;Inert atmosphere;	Compound 23 (4.60g, 30.06mmol) was dissolved in acetonitrile (30mL) was added NIS (7.44g, 33.07 mmol), nitrogen was purged of air and stirred at room temperature for 14 hours under protection. The reaction solution was concentrated, purified by silica gel column chromatography, the mobile phase system methylene chloride and methanol (DCM: MeOH = 50: 1). 5.12 g of a white solid 24 was obtained in a two step yield of 24%.
1.4 g	With N-iodo-succinimide; In acetonitrile; at 60℃; for 10h;	Synthesis of 6-chloro-3-iodoimidazo[l , 2-bJpyridazine To a degassed solution of 6-chloroimidazo[l,2-b]pyridazine (1.0 g, 6.51 mmol) and NIS (2.2 g, 9.77 mmol) in MeCN (30 mL) was heated to 60 C for 10 hours. The reaction mixture was cooled to RT and extract with DCM. The organics were washed with Na2S203 (aq), brine and dried over Na2S04. After concentrated, the crude product was purified by column (PE : EA = 5 : 1) to obtain 6-chloro-3-iodoimidazo[l,2-b]pyridazine (1.4 g, yield: 83%). 1H- MR (CDC13, 400 MHz) delta 7.83 (s, 1H), 7.80 (d, J= 4.8 Hz, 1H), 7.04 (d, J= 9.6 Hz, 1H). MS(M+H)+: 280.

Yield	Reaction Conditions	Operation in experiment
98%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In water; N,N-dimethyl-formamide; at 90℃; for 18h;Inert atmosphere;	Step 1 : To a solution of 6-chloro-3-iodoimidazo[l,2-b]pyridazine (1.00 g, 3.58 mmol) in a mixture of DMF (20 mL) and water (1 mL) under inert atmosphere, were added Na2C03 (759 mg, 7.16 mmol), 4-cyanophenylboronic acid (885 mg, 5.37 mmol) and Pd(PPh3)4 (414 mg, 0.358 mmol). The resulting mixture was stirred at 90 C for 18 h and quenched with ice water. The precipitate was isolated by filtration and dried in vacuo to afford 4-(6- chloroimidazo[l,2-6]pyridazin-3-yl)benzonitrile (897 mg, 98%) as a yellow solid. 1H NMR FontWeight="Bold" FontSize="10" --·.·· (400 MHz, CDC13) delta 8.24-8.21 (m, 2H), 8.18 (s, 1H), 8.02 (d, J= 9.4 Hz, 1H), 7.81-7.79 (m, 2H), 7.45 (d, J = 9.4 Hz, lH); MS (ESI) m/z 255 [C13H7C1N4 + H]+.
98%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In water; N,N-dimethyl-formamide; at 90℃; for 18h;Inert atmosphere;	To a solution of <strong>[923595-49-7]6-chloro-3-iodoimidazo[1,2-b]pyridazine</strong> (1.00 g, 3.58 mmol) in a mixture of DMF (20 mL) and water (1 mL) under inert atmosphere, were added Na2CO3 (759 mg, 7.16 mmol), 4-cyanophenylboronic acid (885 mg, 5.37 mmol) and Pd(PPh3)4 (414 mg, 0.358 mmol). The resulting mixture was stirred at 90 C. for 18 h and quenched with ice water. The precipitate was isolated by filtration and dried in vacuo to afford 4-(6-chloroimidazo[1,2-b]pyridazin-3-yl)benzonitrile (897 mg, 98%) as a yellow solid. 1H NMR (400 MHz, CDCl3) delta 8.24-8.21 (m, 2H), 8.18 (s, 1H), 8.02 (d, J=9.4 Hz, 1H), 7.81-7.79 (m, 2H), 7.45 (d, J=9.4 Hz, 1H); MS (ESI) m/z 255 [C13H7ClN4+H]+.

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H411	Toxic to aquatic life with long-lasting effects
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H420	Harms public health and the environment by destroying ozone in the upper atmosphere

Yield	Reaction Conditions	Operation in experiment
90%	With N-iodo-succinimide; In chloroform; at 20℃;	Preparation of 6-chloro-3-iodoimidazo[1,2-b]pyridazine 6-chloroimidazo[1,2-b]pyridazine (2.0 g, 13.0 mmol, 1.0 equiv) in chloroform (20 mL) at room temperature was added N-iodosuccinimide (2.9 g, 13.0 mmol, 1.0 equiv) then stirred vigorously overnight. The reaction mixture was diluted in water and extracted with ethyl acetate. Purification using column chromatography gave 3.3 g of the yellow solid, 90%: 1H NMR delta 8.21 (d, J=7.6 Hz, 1H), 7.96 (s, 1H), 7.41 (d, J=7.6 Hz, 1H).
90%	With N-iodo-succinimide; In methanol;Reflux;	At room temperature, 294 NIS (1.50 g, 6.50 mmol) was added into the solution of 295 6-chloro-3-imidazo[1,2-b]pyridazine (1.0 g, 6.50 mmol) in 43 methanol (10 mL) in portions, and the reaction was stirred under reflux overnight. The reaction was quenched by adding saturated solution of 178 sodium thiosulfate, extracted with dichloromethane (50 mL×3), the organic layer was combined, washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to afford 1.13 g of a yellow solid. Yield was 90.0%. LC-MS(APCI): m/z=290.1 (M+1)
75%	With iodine; In dimethyl sulfoxide; at 20℃; for 36h;	Example 15 -3 Synthesis of 6-chloro-3-iodo-imidazo[1,2-b]pyridazine 6-chloroimidazo[1,2-b]pyridazine 1a (28.0 g, 0.182 mol) was dissolved in DMSO (196 ml). Iodine (55.0 g, 0.219 mol) was then added and the reaction mixture was stirred at room temperature for 36 hours. The mixture was poured onto a saturated aqueous sodium bicarbonate solution (250 ml) and extracted with dichloromethane (2 x 250ml). The organic layer was washed with an aqueous solution of sodium meta bisulfite (250 ml) followed by brine (250 ml). It was then dried (Na2SO4) and evaporated under reduced pressure. The residue was recrystallised from ethyl acetate to give 23 g (75 %) of 6-chloro-3-iodo-imidazo[1,2-b]pyridazine 5 as an off white solid. 1H-NMR (400 MHz, DMSO-d6) : delta = 8.27 (1 H, d, J = 9.5 Hz), 8.02 (1 H, s), 7.46 (1 H, d, J = 9.5 Hz). LCMS-ESI (m/z); found 280.0 [M+H]+.

[ CAS No. 923595-49-7 ] {[proInfo.proName]}

Quality Control of [ 923595-49-7 ]

Related Doc. of [ 923595-49-7 ]

Product Details of [ 923595-49-7 ]

Calculated chemistry of [ 923595-49-7 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 923595-49-7 ]

Application In Synthesis of [ 923595-49-7 ]

[ 923595-49-7 ] Synthesis Path-Upstream 1~1

[ 923595-49-7 ] Synthesis Path-Downstream 1~88

Precautionary Statements-General

Prevention

Response

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Physical hazards

Health hazards

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