[ CAS No. 166176-46-1 ]

Name: 166176-46-1|Imidazo[1,2-b]pyridazin-3-amine|95%
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Quality Control of [ 166176-46-1 ]

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Product Details of [ 166176-46-1 ]

CAS No. :	166176-46-1	MDL No. :	MFCD09832520
Formula :	C₆H₆N₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	N/A
M.W :	134.14 g/mol	Pubchem ID :	10702308
Synonyms :

Safety of [ 166176-46-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 166176-46-1 ]

Downstream synthetic route of [ 166176-46-1 ]

[ 166176-46-1 ] Synthesis Path-Downstream 1~5

1
[ 1885-14-9 ]
[ 166176-46-1 ]
[ 1229383-63-4 ]

Yield	Reaction Conditions	Operation in experiment
72%	With pyridine In N,N-dimethyl-formamide at 20℃; for 3h;	19 Intermediate 19: lmidazo[1 ,2-bipyridazin-3-yl-carbamic acid phenyl ester.; To a solution of imidazo[1 ,2-b]pyridazin-3-ylamine (209 mg, 1.56 mmol) in dry DMF (5.0 ml_) was added pyridine (382 μl_, 4.68 mmol) and phenyl chloroformate (244 mg, 1.56 mmol). After 3 h at rt, the mixture was diluted with EtOAc (100 ml_) and washed with saturated aqueous NaHCO3 (50 ml_). The organic layer was dried (MgSO4) and concentrated. The residue was purified (FCC) to give imidazo[1 ,2- b]pyridazin-3-yl-carbamic acid phenyl ester (285 mg, 72%). MS (ESI+): calcd for Ci3Hi0N4O2 m/z 254.08, found 255.3 (M+H)+.
72%	With pyridine In N,N-dimethyl-formamide at 20℃; for 3h; Inert atmosphere;	26 Intermediate 26: ImidazoH ^-bipyridazin-S-yl-carbamic acid phenyl ester.; To a solution of imidazo[1 ,2-b]pyhdazin-3-ylamine (209 mg, 1.56 mmol) in dry DMF (5.0 ml_) was added pyridine (382 μl_, 4.68 mmol) and phenyl chloroformate (244 mg, 1.56 mmol). After 3 h at rt, the mixture was diluted with EtOAc (100 ml_) and washed with saturated aqueous NaHCO3 (50 ml_). The organic layer was dried (MgSO4) and concentrated. The residue was purified (FCC) to give imidazo[1 ,2- b]pyridazin-3-yl-carbamic acid phenyl ester (285 mg, 72%). MS (ESI+): calcd for Ci3Hi0N4O2 m/z 254.08, found 255.3 (M+H)+.

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC - WO2010/68452, 2010, A1 Location in patent: Page/Page column 31
[2]Current Patent Assignee: JOHNSON & JOHNSON INC - WO2010/68453, 2010, A1 Location in patent: Page/Page column 37

2
[ 166176-46-1 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1-hydroxy-7-aza-benzotriazole; HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 20 °C 2: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 120 °C

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - US2013/178460, 2013, A1

3
[ 166176-46-1 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 1-hydroxy-7-aza-benzotriazole; HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 20 °C 2: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 120 °C 3: trifluoroacetic acid / dichloromethane / 1 h / 20 °C

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - US2013/178460, 2013, A1

4
[ 1356016-36-8 ]
[ 166176-46-1 ]
[ 1446510-50-4 ]

Yield	Reaction Conditions	Operation in experiment
0.171 g	With 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 2h;	23.1 2-Chloro-thieno[3,2-d]pyrimidine-7-carboxylic acid imidazol[1,2-b]pyridazin-3-ylamide Step 1 2-Chloro-thieno[3,2-d]pyrimidine-7-carboxylic acid imidazol[1,2-b]pyridazin-3-ylamide To a stirred solution of 2-chlorothieno[3,2-d]pyrimidine-7-carboxylic acid (0.100 g, 0.466 mmol) in DMF (4 mL) was added imidazol[1,2-b]pyridazin-3-amine (0.094 g, 0.699 mmol), DIPEA (0.325 mL, 1.86 mmol), 1-hydroxy-7-azabenzotriazole (0.095 g, 0.699 mmol) and HATU (0.266 g, 0.699 mmol). The reaction mixture was stirred at room temperature for 2 h. The reaction mixture was diluted with dichloromethane and water. The organic layer was washed with aqueous sodium carbonate, then brine, and then dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was dried under high vacuum overnight to give 2-chloro-thieno[3,2-d]pyrimidine-7-carboxylic acid imidazol[1,2-b]pyridazin-3-ylamide (0.171 g, 111%) as a yellow solid, which was used directly in the next step without further purification. LCMS m/z [M+H]=331.

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - US2013/178460, 2013, A1 Location in patent: Paragraph 0269

5
[ 2787498-28-4 ]
[ 166176-46-1 ]
[ 2787497-15-6 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 19h; Inert atmosphere;	48; 49 2-(4-Hydroxy-4-methylcyclohexyl)-N-(imidazo[1,2-b]pyridazin-3-yl)-6-methoxy-2H-indazole-5- carboxamide - Isomer 1 (Example 48) & Isomer 2 (Example 49) To a solution of 2-(4-hydroxy-4-methylcyclohexyl)-6-methoxy-2H-indazole-5-carboxylic acid (100 mg, 0.3 mmol) and HATU (150 mg, 0.4 mmol) in DMF (20 mL) at rt under N2 atmosphere was added DIPEA (230 μL, 1.3 mmol), followed by the addition of imidazo[1,2-b]pyridazin-3-amine (53 mg, 0.4 mmol). The reaction mixture was stirred at rt for 19 h. The crude was purified directly by C18-flash chromatography (eluting with 0 - 100% MeCN in water (0.05% NH4OH)), followed by chiral prep. HPLC (Chiralpak ID, 5 μm 20 mm × 250 mm; isocratic with 20% MTBE (0.1% 2N NH3-MeOH) in DCM/MeOH (1:1) in 12 min; 20.0 mL/min) to afford 2-(4-hydroxy-4-methylcyclohexyl)-N-(imidazo[1,2-b]pyridazin- 3-yl)-6-methoxy-2H-indazole-5-carboxamide - Isomer 1 (11 mg, 8%, 100%ee) and 2-(4-hydroxy-4- methylcyclohexyl)-N-(imidazo[1,2-b]pyridazin-3-yl)-6-methoxy-2H-indazole-5-carboxamide -Isomer 2 (7 mg, 5%, 99.9%ee), both as yellow solids. Isomer 1: 1H NMR (400 MHz, DMSO-d6) δ 11.05 (s, 1H), 8.61 - 8.67 (m, 1H), 8.58 (s, 2H), 8.14 (dd, 1H), 8.05 (s, 1H), 7.25 (s, 1H), 7.21 (dd, 1H), 4.34 - 4.48 (m, 1H), 4.27 (s, 1H), 4.12 (s, 3H), 2.18 - 2.35 (m, 2H), 1.82 - 1.94 (m, 2H), 1.62 - 1.76 (m, 2H), 1.44 - 1.6 (m, 2H), 1.17 (s, 3H). MS ESI, m/z = 421 [M+H]+. Isomer 2: 1H NMR (400 MHz, DMSO-d6) δ 11.04 (s, 1H), 8.60 - 8.68 (m, 2H), 8.57 (s, 1H), 8.14 (d, 1H), 8.05 (s, 1H), 7.27 (s, 1H), 7.21 (ddd, 1H), 4.44 - 4.56 (m, 2H), 4.11 (s, 3H), 1.98 - 2.12 (m, 4H), 1.53 - 1.73 (m, 4H), 1.23 (s, 3H). MS ESI, m/z = 421 [M+H]+
	With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 19h; Inert atmosphere;	48; 49 2-(4-Hydroxy-4-methylcyclohexyl)-N-(imidazo[1,2-b]pyridazin-3-yl)-6-methoxy-2H-indazole-5- carboxamide - Isomer 1 (Example 48) & Isomer 2 (Example 49) To a solution of 2-(4-hydroxy-4-methylcyclohexyl)-6-methoxy-2H-indazole-5-carboxylic acid (100 mg, 0.3 mmol) and HATU (150 mg, 0.4 mmol) in DMF (20 mL) at rt under N2 atmosphere was added DIPEA (230 μL, 1.3 mmol), followed by the addition of imidazo[1,2-b]pyridazin-3-amine (53 mg, 0.4 mmol). The reaction mixture was stirred at rt for 19 h. The crude was purified directly by C18-flash chromatography (eluting with 0 - 100% MeCN in water (0.05% NH4OH)), followed by chiral prep. HPLC (Chiralpak ID, 5 μm 20 mm × 250 mm; isocratic with 20% MTBE (0.1% 2N NH3-MeOH) in DCM/MeOH (1:1) in 12 min; 20.0 mL/min) to afford 2-(4-hydroxy-4-methylcyclohexyl)-N-(imidazo[1,2-b]pyridazin- 3-yl)-6-methoxy-2H-indazole-5-carboxamide - Isomer 1 (11 mg, 8%, 100%ee) and 2-(4-hydroxy-4- methylcyclohexyl)-N-(imidazo[1,2-b]pyridazin-3-yl)-6-methoxy-2H-indazole-5-carboxamide -Isomer 2 (7 mg, 5%, 99.9%ee), both as yellow solids. Isomer 1: 1H NMR (400 MHz, DMSO-d6) δ 11.05 (s, 1H), 8.61 - 8.67 (m, 1H), 8.58 (s, 2H), 8.14 (dd, 1H), 8.05 (s, 1H), 7.25 (s, 1H), 7.21 (dd, 1H), 4.34 - 4.48 (m, 1H), 4.27 (s, 1H), 4.12 (s, 3H), 2.18 - 2.35 (m, 2H), 1.82 - 1.94 (m, 2H), 1.62 - 1.76 (m, 2H), 1.44 - 1.6 (m, 2H), 1.17 (s, 3H). MS ESI, m/z = 421 [M+H]+. Isomer 2: 1H NMR (400 MHz, DMSO-d6) δ 11.04 (s, 1H), 8.60 - 8.68 (m, 2H), 8.57 (s, 1H), 8.14 (d, 1H), 8.05 (s, 1H), 7.27 (s, 1H), 7.21 (ddd, 1H), 4.44 - 4.56 (m, 2H), 4.11 (s, 3H), 1.98 - 2.12 (m, 4H), 1.53 - 1.73 (m, 4H), 1.23 (s, 3H). MS ESI, m/z = 421 [M+H]+

Reference： [1]Current Patent Assignee: ASTRAZENECA PLC - WO2022/122876, 2022, A1 Location in patent: Page/Page column 95; 97; 98
[2]Current Patent Assignee: ASTRAZENECA PLC - WO2022/122876, 2022, A1 Location in patent: Page/Page column 95; 97; 98

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P222	Do not allow contact with air.
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P230	Keep wetted
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P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
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P342	If experiencing respiratory symptoms:
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P361	Remove/Take off immediately all contaminated clothing.
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P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
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P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
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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
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H228	Flammable solid
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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. 166176-46-1 ]

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Application In Synthesis of [ 166176-46-1 ]

[ 166176-46-1 ] Synthesis Path-Downstream 1~5

Related Functional Groups of [ 166176-46-1 ]

Amines

Related Parent Nucleus of [ 166176-46-1 ]

Other Aromatic Heterocycles

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[ 166176-46-1 ]

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[ 166176-46-1 ]