1240518-54-0|3-Amino-1H-indazole-4-carbonitrile| Ambeed

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Quality Control of [ 1240518-54-0 ] Purity: 95% SDS Specification

COA

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NMR

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CNMR

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LC-MS

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Product Details of [ 1240518-54-0 ]

CAS No. :	1240518-54-0
Formula :	C₈H₆N₄
M.W :	158.16
SMILES Code :	N#CC1=CC=CC2=C1C(N)=NN2
MDL No. :	MFCD20486223
InChI Key :	KVXRKRURRSOVSJ-UHFFFAOYSA-N
Pubchem ID :	54016394

Safety of [ 1240518-54-0 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 1240518-54-0 ]

* 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.

Downstream synthetic route of [ 1240518-54-0 ]

[ 1240518-54-0 ] Synthesis Path-Downstream 1~27

1
[ 24424-99-5 ]
[ 1240518-54-0 ]
[ 1240518-55-1 ]

Yield	Reaction Conditions	Operation in experiment
56%	With dmap; triethylamine; In acetonitrile; for 0.5h;Inert atmosphere;	Intermediate 631,1-Dimethylethyl 3-amino-4-cyano-1H-indazole-1-carboxylate; Di-tert-butyl dicarbonate (7.13 g, 32.7 mmol) in dichloromethane (150 mL) was added to a solution of <strong>[1240518-54-0]3-amino-1H-indazole-4-carbonitrile</strong> (for a preparation see Intermediate 62) (4.7 g, 29.7 mmol), 4-dimethylaminopyridine (0.726 g, 5.94 mmol) and triethylamine (8.28 mL, 59.4 mmol) in acetonitrile (150 mL) and stirred for 0.5 h under nitrogen. LCMS showed no starting material remaining so the reaction mixture was concentrated in vacuo to give a residue which was partitioned between DCM (250 mL) and water (250 mL). The organic layer was washed a further two times with water (250 mL) and once with brine (200 mL) before being dried over anhydrous magnesium sulfate and evaporated in vacuo to give the title compound (4.3 g, 56%) as a yellow solid. LCMS (System A): RT=0.94 min, ES+ve m/z 259 (M+H)+.

References: [1]Patent: US2010/216860,2010,A1 .Location in patent: Page/Page column 33.
[2]Journal of Medicinal Chemistry,2013,vol. 56,p. 1946 - 1960.

2
[ 65610-13-1 ]
[ 1240518-54-0 ]

Yield	Reaction Conditions	Operation in experiment
87%	With hydrazine hydrate; In ethanol; at 70.0℃;	Intermediate 623-Amino-1H-indazole-4-carbonitrile; 3-Fluoro-1,2-benzenedicarbonitrile (APIN) (5 g, 34.2 mmol) was dissolved in ethanol (80 mL) and hydrazine monohydrate (4.98 mL, 103 mmol) was added to the solution. The reaction was heated at 70 C. overnight. The reaction mixture was concentrated in vacuo and the residue was partitioned between ethyl acetate (200 mL) and water (200 mL). The organic layer was washed with water (100 mL). The aqueous layers were extracted with ethyl acetate (200 mL). Organic layers were combined, dried over anhydrous magnesium sulfate and evaporated in vacuo to give the title compound (4.7 g, 87%) as a yellow solid. LCMS (System A) RT=0.53 min, ES+ve m/z 159 (M+H)+.
47%	With hydrazine hydrate; In ethanol; at 70.0℃; for 8h;	3-Fluorophthalonitrile (1.00 g, 6.84 mmol) was dissolved in ethanol (10 mL) and treated with hydrazine hydrate (1.37 g, 27.4 mmol). After stirring at 70 C for 8 h, the mixture was cooled to RT and concentrated in vacuo. The residue was dissolved in a mixture of water and ethyl acetate. The aqueous layer was extracted once more with ethyl acetate. The combined organic layers were washed with water and with brine, dried over magnesium sulfate, concentrated in vacuo and dried to yield the title compound (0.51 g, 47% of theory) LC-MS (Method 2B): Rt = 1.47 min, MS (ESIPos): m/z = 159 [M+H]+
0.51 g	With hydrazine hydrate; In ethanol; at 70.0℃; for 8h;	Example 77A 3-Amino-1H-indazole-4-carbonitrile 3-Fluorophthalonitrile (1.00 g, 6.84 mmol) was dissolved in ethanol (10 mL) and treated with hydrazine hydrate (1.37 g, 27.4 mmol). After stirring at 70 C. for 8 h, the mixture was cooled to RT and concentrated in vacuo. The residue was dissolved in a mixture of water and ethyl acetate. The aqueous layer was extracted once more with ethyl acetate. The combined organic layers were washed with water and with brine, dried over magnesium sulfate, concentrated in vacuo and dried to yield the title compound (0.51 g, 47% of theory) LC-MS (Method 2B): Rt=1.47 min, MS (ESIPos): m/z=159 [M+H]+

References: [1]Patent: US2010/216860,2010,A1 .Location in patent: Page/Page column 32.
[2]Journal of Medicinal Chemistry,2013,vol. 56,p. 1946 - 1960.
[3]Patent: WO2015/67549,2015,A1 .Location in patent: Page/Page column 105.
[4]Patent: US2015/126449,2015,A1 .Location in patent: Paragraph 0578 - 0580.

3
[ 1240518-54-0 ]
[ 64407-07-4 ]
C₁₆H₁₁N₅ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 1946 - 1960.

4
[ 1240518-54-0 ]
[ 1240517-77-4 ]

References: [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 1946 - 1960.

5
[ 1240518-54-0 ]
C₂₆H₂₂Cl₂N₄O₆S₄ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 1946 - 1960.

6
[ 1240518-54-0 ]
[ 1240518-66-4 ]

References: [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 1946 - 1960.
[2]Journal of Medicinal Chemistry,2013,vol. 56,p. 1946 - 1960.

7
[ 1240518-54-0 ]
[ 1240517-78-5 ]

References: [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 1946 - 1960.
[2]Journal of Medicinal Chemistry,2013,vol. 56,p. 1946 - 1960.

8
[ 1240518-54-0 ]
[ 1240517-79-6 ]

References: [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 1946 - 1960.
[2]Journal of Medicinal Chemistry,2013,vol. 56,p. 1946 - 1960.

9
[ 1240518-54-0 ]
[ 1240517-76-3 ]

References: [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 1946 - 1960.

10
[ 1240518-54-0 ]
[ 1240518-81-3 ]

References: [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 1946 - 1960.

11
[ 1240518-54-0 ]
C₂₀H₁₂ClN₅O₂S₂ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 1946 - 1960.

12
[ 1240518-54-0 ]
[ 1240518-84-6 ]

References: [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 1946 - 1960.
[2]Journal of Medicinal Chemistry,2013,vol. 56,p. 1946 - 1960.

13
[ 1240518-54-0 ]
[ 1240518-65-3 ]

References: [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 1946 - 1960.
[2]Journal of Medicinal Chemistry,2013,vol. 56,p. 1946 - 1960.

14
[ 1240518-54-0 ]
[ 1240518-56-2 ]

References: [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 1946 - 1960.

15
[ 1240518-54-0 ]
[ 1240518-57-3 ]

References: [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 1946 - 1960.

16
[ 1240518-54-0 ]
[ 1240518-58-4 ]

References: [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 1946 - 1960.

17
[ 1240518-54-0 ]
[ 1240518-64-2 ]

References: [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 1946 - 1960.

18
[ 1240518-54-0 ]
[ 1240518-59-5 ]

References: [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 1946 - 1960.

19
[ 1240518-54-0 ]
[ 1240518-62-0 ]

References: [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 1946 - 1960.

20
[ 1240518-54-0 ]
[ 1240518-63-1 ]

References: [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 1946 - 1960.

21
[ 1240518-54-0 ]
[ 1240518-60-8 ]

References: [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 1946 - 1960.

22
[ 1240518-54-0 ]
[ 1240518-61-9 ]

References: [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 1946 - 1960.

23
[ 1240518-54-0 ]
4-[1-(tert-butoxycarbonyl)piperidin-4-yl]-2-oxo-1,2-dihydropyrimido[1,2-b]indazole-10-carboxylic acid [ No CAS ]

References: [1]Patent: US2015/126449,2015,A1 .
[2]Patent: WO2015/67549,2015,A1 .

24
[ 1240518-54-0 ]
2-oxo-4-(piperidin-4-yl)-1,2-dihydropyrimido[1,2-b]indazole-10-carbonitrile trifluoroacetate [ No CAS ]

References: [1]Patent: US2015/126449,2015,A1 .
[2]Patent: WO2015/67549,2015,A1 .

25
[ 1240518-54-0 ]
[ 1336874-02-2 ]
tert-butyl 4-(10-cyano-2-oxo-1,2-dihydropyrimido[1,2-b]indazol-4-yl)piperidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
25%		3-Amino-lH-indazole-4-carbonitrile (0.51 g, 3.20 mmol) and tert-butyl 4-[(2,2-dimethyl-4,6-dioxo-l,3- dioxan-5-yl)carbonyl]piperidine-l -carboxylate (1.27 g, 3.55 mmol) were dissolved in acetonitrile (20 mL) and refluxed for 6 h. After cooling to RT, the solvent was removed in vacuo and the residue was dissolved in l-methoxy-2-propanol (20 mL). Potassium phosphate (1.37 g, 6.45 mmol) was added and the mixture was stirred at 80 C for 6 h. Concentration in vacuo and purification by preparative HPLC (Method 1A) afforded the title compound (0.32 g, 25% of theory). LC-MS (Method IB): Rt = 1.07 min, MS (ESIPos): m/z = 394 [M+H]+
25%		3-Amino-li7-indazole-4-carbonitrile (0.51 g, 3.20 mmol) and ieri-butyl 4-[(2,2-dimethyl-4,6-dioxo-l,3- dioxan-5-yl)carbonyl]piperidine-l-carboxylate (1.27 g, 3.55 mmol) were dissolved in acetonitrile (20 mL) and refluxed for 6 h. After cooling to RT, the solvent was removed in vacuo and the residue was dissolved in l-methoxy-2-propanol (20 mL). Potassium phosphate (1.37 g, 6.45 mmol) was added and the mixture was stirred at 80 C for 6 h. Concentration in vacuo and purification by preparative HPLC (Method 1A) afforded the title compound (0.32 g, 25% of theory). LC-MS (Method IB): Rt = 1.07 min, MS (ESIPos): m/z = 394 [M+H]+
0.32 g	With potassium phosphate; In acetonitrile; for 6h;Reflux;	Example 78A Tert-butyl 4-(10-cyano-2-oxo-1,2-dihydropyrimido[1,2-b]indazol-4-yl)piperidine-1-carboxylate 3-Amino-1H-indazole-4-carbonitrile (0.51 g, 3.20 mmol) and tert-butyl 4-[(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)carbonyl]piperidine-1-carboxylate (1.27 g, 3.55 mmol) were dissolved in acetonitrile (20 mL) and refluxed for 6 h. After cooling to RT, the solvent was removed in vacuo and the residue was dissolved in 1-methoxy-2-propanol (20 mL). Potassium phosphate (1.37 g, 6.45 mmol) was added and the mixture was stirred at 80 C. for 6 h. Concentration in vacuo and purification by preparative HPLC (Method 1A) afforded the title compound (0.32 g, 25% of theory). LC-MS (Method 1B): Rt=1.07 min, MS (ESIPos): m/z=394 [M+H]+

References: [1]Patent: WO2015/67549,2015,A1 .Location in patent: Page/Page column 106.
[2]Patent: WO2016/173948,2016,A1 .Location in patent: Page/Page column 177.
[3]Patent: US2015/126449,2015,A1 .Location in patent: Paragraph 0581 - 0583.

26
[ 1240518-54-0 ]
2-oxo-4-(piperidin-4-yl)-1,2-dihydropyrimido[1,2-b]indazole-10-carbonitrile hydrochloride [ No CAS ]

References: [1]Patent: WO2015/67549,2015,A1 .

27
[ 1240518-54-0 ]
2-oxo-4-(piperidin-4-yl)-1,2-dihydropyrimido[1,2-b]indazole-10-carboxylic acid hydrochloride [ No CAS ]

References: [1]Patent: WO2015/67549,2015,A1 .

Historical Records

Technical Information

• Blaise Reaction • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Catalytic Hydrogenation • Chan-Lam Coupling Reaction • Complex Metal Hydride Reductions • Hydride Reductions • Leuckart-Wallach Reaction • Mannich Reaction • Petasis Reaction • Preparation of Aldehydes and Ketones • Preparation of Amines • Reactions of Amines • Ritter Reaction • Specialized Acylation Reagents-Vilsmeier Reagent • Thorpe-Ziegler Reaction • Ugi Reaction

Precautionary Statements-General
Code	Phrase
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Code	Phrase
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P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
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P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
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P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
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.
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.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
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:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
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P401
P402	Store in a dry place.
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P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
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P501	Dispose of contents/container to ...
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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
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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
H350	May cause cancer
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

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CAS No.: 1240518-54-0

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CAS No.: 1240518-54-0

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Product Details of [ 1240518-54-0 ]

Safety of [ 1240518-54-0 ]

Application In Synthesis of [ 1240518-54-0 ]

[ 1240518-54-0 ] Synthesis Path-Downstream 1~27

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Technical Information

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Precautionary Statements-General

Prevention

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Physical hazards

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