[ CAS No. 675580-49-1 ]

Name: 675580-49-1|(6-Chloroimidazo[1,2-b]pyridazin-3-yl)methanol|96%
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Quality Control of [ 675580-49-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 675580-49-1 ]

SDS Specification

Alternatived Products of [ 675580-49-1 ]

Product Details of [ 675580-49-1 ]

CAS No. :	675580-49-1	MDL No. :	MFCD11044752
Formula :	C₇H₆ClN₃O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VZFRNQCOHYEZFL-UHFFFAOYSA-N
M.W :	183.60	Pubchem ID :	57352521
Synonyms :

Calculated chemistry of [ 675580-49-1 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.14
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	44.12
TPSA :	50.42 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) :	-7.11 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.51
Log Po/w (XLOGP3) :	0.44
Log Po/w (WLOGP) :	0.72
Log Po/w (MLOGP) :	0.67
Log Po/w (SILICOS-IT) :	0.91
Consensus Log Po/w :	0.85

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.74
Solubility :	3.31 mg/ml ; 0.018 mol/l
Class :	Very soluble
Log S (Ali) :	-1.07
Solubility :	15.7 mg/ml ; 0.0858 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.16
Solubility :	1.27 mg/ml ; 0.00693 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.14

Safety of [ 675580-49-1 ]

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

Application In Synthesis of [ 675580-49-1 ]

* 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 [ 675580-49-1 ]
Downstream synthetic route of [ 675580-49-1 ]

[ 675580-49-1 ] Synthesis Path-Upstream 1~1

1
[ 50-00-0 ]
[ 6775-78-6 ]
[ 675580-49-1 ]

Yield	Reaction Conditions	Operation in experiment
72%	Stage #1: Reflux	Intermediate C6-Chloro-imidazo[1 ,2-b]pyridazine-3-carbaldehyde I Intermediate C(6-Chloro-imidazo[1 ,2-b]pyridazin-3-yl)-methanol (i) To a solution of 6-chloroimidazo[1 ,2-b]pyridazine (1.5 g, 9.8 mmol) in AcOH (50 ml.) was added NaOAc (1.4 g, 17.1 mmol) and paraformaldehyde (1.5 g). The mixture was heated at reflux overnight and then concentrated under reduced pressure. The residue was basified to pH = 12. Then the mixture was filtered and the solid was washed with EtOH to afford (6- chloro-imidazo[1 ,2-b]pyridazin-3-yl)-methanol (1.3 g) in 72percent yield.
72%	With sodium acetate In acetic acidReflux	To a solution of 6-chloroimidazo[1 ,2-b]pyridazine (1 .5 g, 9.8 mmol) in AcOH (50 ml_) was added NaOAc (1 .4 g, 17.1 mmol) and paraformaldehyde (1.5 g). The mixture was heated at reflux overnight and concentrated under reduced pressure. The residue was basified to pH 12. Then the mixture was filtered and the solid was washed with EtOH to afford (6-chloro- imidazo[1 ,2-b]pyridazin-3-yl)-methanol (1.3 g) in 72percent yield.

Reference： [1] Patent: WO2011/18454, 2011, A1, . Location in patent: Page/Page column 55
[2] Patent: WO2011/20861, 2011, A1, . Location in patent: Page/Page column 66

[ 675580-49-1 ] Synthesis Path-Downstream 1~5

1
[ 675580-49-1 ]
[ 98-80-6 ]
[ 1002309-36-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; water; at 80.0℃; for 1.0h;	To a mixture of (6-chloroimidazo [1, 2-b] pyridazin-3 -yl) methanol (see Galtier, C. et al, Antiviral Chemistry & Chemotherapy, 2003, 14, 177-182) (0.200 g, 1.09 mmol) , phenylboronic acid (0.133 g, 1.09 mmol), PdCl2 (dppf) -CH2Cl2 (0.0445 g, 0.0545 mmol) in dioxane was added sat NaHCO3 (1.20 ml, >2.40 mmol) . The mixture was blanketed with N2, the vessel sealed and heated at 80 C for 1 h. The mixture was allowed to cool to rt and diluted with EtOAc. The organic phase was washed with water, then sat. NaHCO3, dried over Na2SO4, filtered and evaporated. The mixture was purified via flash chromatography using a gradient of 0 % to 10 % MeOH in EtOAc. The title compound was collected as a white solid.

Reference： [1]Patent: WO2008/8539,2008,A2 .Location in patent: Page/Page column 107

2
[ 675580-49-1 ]
[ 75-03-6 ]
[ 74-88-4 ]
[ 1034622-46-2 ]
[ 1034622-49-5 ]

Yield	Reaction Conditions	Operation in experiment
51%; 53%	With sodium hydride; In N,N-dimethyl-formamide; for 2.0h;	(6-Chloroimidazo[1,2-b]pyridazin-3-yl)methanol 72 (1 mmol) and the alkyl iodide (1.1 mmol) were dissolved in dry DMF (2 mL) and sodium hydride (60% disp, 1.1 mmol) added. After 2 h the mixture was poured into water and extracted (2×) with ethyl acetate. The combined organic layers were washed with 5% lithium chloride solution (5×), dried, concentrated and the residue purified by column chromatography (12 g ISCO column eluting with methylene chloride and a methanol/ammonia mixture (10:1); gradient 100% methylene chloride to 80% methylene chloride over 30 min at 25 mL/min) to provide the desired product 8.8a 6-Chloro-3-(methoxymethyl)imidazo[1,2-b]pyridazine was obtained as a yellow oil (100 mg, 51%); Rf=0.90 (CH2Cl2/MeOH/NH4OH, 160:18:2); 1H NMR (500 MHz, CD3OD) delta 8.05 (d, J=9.5 Hz, 1H), 7.81 (s, 1H), 7.34 (d, J=9.5 Hz, 1H), 4.85 (s, 2H), 3.41 (s, 3H).8b 6-Chloro-3-(ethoxymethyl)imidazo[1,2-b]pyridazine was obtained as a yellow oil (111 mg, 53%); Rf=0.90 (CH2Cl2/MeOH/NH4OH, 160:18:2); 1H NMR (500 MHz, CD3OD) delta 8.01 (d, J=9.5 Hz, 1H), 7.80 (s, 1H), 7.34 (d, J=9.5 Hz, 1H), 4.87 (s, 2H), 3.63 (quart, J=7.0 Hz, 2H), 1.21 (t, J=7.0 Hz, 3H).

Reference： [1]Patent: US2008/153813,2008,A1 .Location in patent: Page/Page column 5

3
[ 50-00-0 ]
[ 6775-78-6 ]
[ 675580-49-1 ]

Yield	Reaction Conditions	Operation in experiment
72%		Intermediate C6-Chloro-imidazo[1 ,2-b]pyridazine-3-carbaldehyde I Intermediate C(6-Chloro-imidazo[1 ,2-b]pyridazin-3-yl)-methanol (i) To a solution of 6-chloroimidazo[1 ,2-b]pyridazine (1.5 g, 9.8 mmol) in AcOH (50 ml.) was added NaOAc (1.4 g, 17.1 mmol) and paraformaldehyde (1.5 g). The mixture was heated at reflux overnight and then concentrated under reduced pressure. The residue was basified to pH = 12. Then the mixture was filtered and the solid was washed with EtOH to afford (6- chloro-imidazo[1 ,2-b]pyridazin-3-yl)-methanol (1.3 g) in 72% yield.
72%	With sodium acetate; In acetic acid;Reflux;	To a solution of 6-chloroimidazo[1 ,2-b]pyridazine (1 .5 g, 9.8 mmol) in AcOH (50 ml_) was added NaOAc (1 .4 g, 17.1 mmol) and paraformaldehyde (1.5 g). The mixture was heated at reflux overnight and concentrated under reduced pressure. The residue was basified to pH 12. Then the mixture was filtered and the solid was washed with EtOH to afford (6-chloro- imidazo[1 ,2-b]pyridazin-3-yl)-methanol (1.3 g) in 72% yield.

Reference： [1]Patent: WO2011/18454,2011,A1 .Location in patent: Page/Page column 55
[2]Patent: WO2011/20861,2011,A1 .Location in patent: Page/Page column 66

4
[ 675580-49-1 ]
6-chloroimidazo[1,2-b]pyridazine-3-carbaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%	With manganese(IV) oxide; In dichloromethane; at 20.0℃;	6-Chloro-imidazo[1 ,2-b]pyridazine-3-carbaldehyde (intermediate C) To a solution of (6-chloro-imidazo[1 ,2-b]pyridazin-3-yl)-methanol (1.3 g, 7.1 mmol) in DCM (50 ml.) was added active MnO2 (3 g, 34.5 mmol). The mixture was stirred at rt overnight and then filtered. The filtrate was concentrated under vacuum and the residue was washed with EtOAc to afford 6-chloro-imidazo[1 ,2-b]pyridazine-3-carbaldehyde (0.7 g) in 54% yield. 1H- NMR (400MHz, CDCI3) delta 10.36 (s, 1 H), 8.42 (s, 1 H), 8.08 (d, 1 H), 7.38 (d, 1 H).
54%	With manganese(IV) oxide; In dichloromethane; at 20.0℃;	To a solution of (6-chloro-imidazo[1 ,2-b]pyridazin-3-yl)-methanol (1.3 g, 7.1 mmol) in DCM (50 ml_) was added active MnO2 (3 g, 34.5 mmol). The mixture was stirred at rt overnight and filtered. The filtrate was concentrated under vacuum and the residue was washed with EtOAc to affrode 6-chloro-imidazo[1 ,2-b]pyridazine-3-carbaldehyde (0.7 g) in 54% yield. 1H- NMR (400MHz, CDCI3) delta ppm 10.36 (s, 1 H), 8.42 (s, 1 H), 8.08 (d, 1 H), 7.38 (d, 1 H).

Reference： [1]Patent: WO2011/18454,2011,A1 .Location in patent: Page/Page column 55-56
[2]Patent: WO2011/20861,2011,A1 .Location in patent: Page/Page column 66

5
6-chloroimidazo[1,2-b]pyridazine-3-carbaldehyde [ No CAS ]
[ 675580-49-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tetrahydroborate; In methanol; at 20.0℃; for 0.5h;	To a solution of 6-chloroimidazo[1,2-b]pyridazine-3-carbaldehyde (0.55 g, 3 mmol) inmethanol (20 ml) was added sodium borohydride (0.15 g, 4 mmol) in a small portions at rt. After25 stirring at rt for 30 min, the reaction was quenched with water, and extracted with DCM to give crudeproduct (0.55 g, 100% yield). 40 mg of crude product was purified by Prep HPLC to give (6-chloroimidazo[1,2-b]pyridazin-3-yl)methanol as a white solid. 1H NMR (400 MHz, CHLOROFORM-d) 8 ppm 7.95 (d, J=9.35 Hz, 1 H), 7.79 (s, 1 H), 7.11 (d, J=9.35 Hz, 1 H), 5.07 (s, 2 H); LRMS (ESI) mje184.0 [(M + H)+, calcd for C7H7CIN30 184.6].

Reference： [1]Patent: WO2013/134219,2013,A1 .Location in patent: Page/Page column 108; 109

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P337 + P313	IF eye irritation persists: Get medical advice/attention.
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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
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H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 675580-49-1 ]

Quality Control of [ 675580-49-1 ]

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Product Details of [ 675580-49-1 ]

Calculated chemistry of [ 675580-49-1 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 675580-49-1 ]

Application In Synthesis of [ 675580-49-1 ]

[ 675580-49-1 ] Synthesis Path-Upstream 1~1

[ 675580-49-1 ] Synthesis Path-Downstream 1~5

Related Functional Groups of [ 675580-49-1 ]

Chlorides

Alcohols

Related Parent Nucleus of [ 675580-49-1 ]

Other Aromatic Heterocycles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 675580-49-1 ]

Related Parent Nucleus of
[ 675580-49-1 ]