[ CAS No. 166176-46-1 ]

Name: 166176-46-1|Imidazo[1,2-b]pyridazin-3-amine|95%
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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 1~4

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

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P322
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P342	If experiencing respiratory symptoms:
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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.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
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P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
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.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
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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
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H261	In contact with water releases flammable gas
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H301	Toxic if swallowed
H302	Harmful if swallowed
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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
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H336	May cause drowsiness or dizziness
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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 ]

Quality Control of [ 166176-46-1 ]

Related Doc. of [ 166176-46-1 ]

Product Details of [ 166176-46-1 ]

Safety of [ 166176-46-1 ]

Application In Synthesis of [ 166176-46-1 ]

[ 166176-46-1 ] Synthesis Path-Downstream 1~4

Related Functional Groups of [ 166176-46-1 ]

Amines

Related Parent Nucleus of [ 166176-46-1 ]

Other Aromatic Heterocycles

Precautionary Statements-General

Prevention

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Physical hazards

Health hazards

Environmental hazards

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Related Functional Groups of
[ 166176-46-1 ]

Related Parent Nucleus of
[ 166176-46-1 ]