[ CAS No. 114474-28-1 ]

Name: 4-(1H-Pyrazol-4-yl)aniline
Brand: Ambeed
SKU: A105393
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Quality Control of [ 114474-28-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 114474-28-1 ]

SDS

Alternatived Products of [ 114474-28-1 ]

Product Details of [ 114474-28-1 ]

CAS No. :	114474-28-1	MDL No. :	MFCD11932600
Formula :	C₉H₉N₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	159.19	Pubchem ID :	13977013
Synonyms :

Computed Properties of [ 114474-28-1 ]

TPSA :Topological Polar Surface Area	54.7	H-Bond Acceptor Count :	2
XLogP3 :	1.2	H-Bond Donor Count :	2
SP3 :	0.00	Rotatable Bond Count :	1

Safety of [ 114474-28-1 ]

Signal Word:	Warning	Class	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 114474-28-1 ]

Upstream synthesis route of [ 114474-28-1 ]
Downstream synthetic route of [ 114474-28-1 ]

[ 114474-28-1 ] Synthesis Path-Upstream 1~4

1
[ 114474-26-9 ]
[ 114474-28-1 ]

Yield	Reaction Conditions	Operation in experiment
94%	at 20℃;	To a suspension of 4-(4-Nitrophenyl)-1H-pyrazole (8.3 g, 43.88 mmol) in MeOH/DME (2:1 v/v) was added 10percent Pd/C (wet, 415 mg). The reaction flask was purged with vacuum then filled with H2 from a balloon. This was done a total of 3 times. The reaction mixture was stirred at rt and checked by LC-MS for formation of the amine. After stirring for 2.5 at rt, LC-MS and tlc showed that there is a minor amount of SM in the reaction. An additional amount of catalyst (200 mg) was added to the reaction mixture and the reaction vessel was filled with H2 as before. The reaction was checked after 2h for disappearance of the remaining SM. At this time, the reaction was complete. The mixture was filtered on Celite and the Celite was washed with MeOH. The solvent was removed in vacuo to give 6.59 g (94percent) of a yellow solid. ‘H NIVIR (400 MHz, DMSO-d6) ö 12.68 (b, 1H), 7.80 (s, 2H), 7.23 (d, J = 8.0 Hz, 2H), 6.54 (d, J = 8.0 Hz, 2H), 4.97 (s, 2H). MS (ES+) m/e 160 (M+H)+.
94%	With palladium 10% on activated carbon; hydrogen In methanol; 1,2-dimethoxyethane at 20℃; for 2.00 h;	[0092] To a suspension of 4-(4-Nitrophenyl)-lH-pyrazole (8.3 g, 43.88 mmol) in MeOH/DME (2: 1 v/v) was added 10percent Pd/C (wet, 415 mg). The reaction flask was purged with vacuum then filled with from a balloon. This was done a total of 3 times. The reaction mixture was stirred at rt and checked by LC-MS for formation of the amine. After stirring for 2.5 at rt, LC-MS and tic showed that there is a minor amount of SM in the reaction. An additional amount of catalyst (200 mg) was added to the reaction mixture and the reaction vessel was filled with as before. The reaction was checked after 2h for disappearance of the remaining SM. At this time, the reaction was complete. The mixture was filtered on Celite and the Celite was washed with MeOH. The solvent was removed in vacuo to give 6.59 g (94percent) of a yellow solid. 1H NMR (400 MHz, DMSO-d₆) δ 12.68 (b, 1H), 7.80 (s, 2H), 7.23 (d, J = 8.0 Hz, 2H), 6.54 (d, J = 8.0 Hz, 2H), 4.97 (s, 2H). MS (ES+) m/e 160 (M+H)+.

Reference： [1] Patent: WO2016/210331, 2016, A1. Location in patent: Paragraph 0087; 0088
[2] Patent: WO2016/210330, 2016, A1. Location in patent: Paragraph 0091-0092
[3] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1987, vol. 26, # 1-12, p. 616 - 619

2
[ 104-03-0 ]
[ 114474-28-1 ]

Reference： [1] Patent: WO2016/210331, 2016, A1
[2] Patent: WO2016/210330, 2016, A1

3
[ 676605-99-5 ]
[ 114474-28-1 ]

Reference： [1] Patent: WO2016/210331, 2016, A1
[2] Patent: WO2016/210330, 2016, A1

4
[ 93072-94-7 ]
[ 114474-28-1 ]

Reference： [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1987, vol. 26, # 1-12, p. 616 - 619

[ 114474-28-1 ] Synthesis Path-Downstream 1~10

1
2-chloro-4-(1-ethyl-3-(pyridin-3-yl)-1H-pyrazol-4-yl)pyrimidine [ No CAS ]
[ 114474-28-1 ]
N-(4-(1H-pyrazol-4-yl)phenyl)-4-(1-ethyl-3-(pyridin-3-yl)-1H-pyrazol-4-yl)pyrimidin-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61 mg	In methanol; at 90.0℃;	A mixture containing <strong>[114474-28-1]4-(1H-pyrazol-4-yl)aniline</strong> (77 mg), 2-chloro-4-(1-ethyl-3-(pyridin-3-yl)-1H-pyrazol-4-yl)pyrimidine (Production Example 3, 115 mg)and methanol (0.5 mL) was stirred at 90 C. overnight. The reaction mixture was concentrated under a reduced pressure, the obtained residue was purified through silica gel column chromatography (elution solvent: dichloromethane-methanol), and thereby N-(4-(1H-pyrazol-4-yl)phenyl)-4-(1-ethyl-3-(pyridin-3-yl)-1H-pyrazol-4-yl)pyrimidin-2-amine (61 mg)as a yellow solid was obtained.

Reference： [1]Patent: US2019/337926,2019,A1.Location in patent: Paragraph 0692-0693

2
[ 4755-77-5 ]
[ 114474-28-1 ]
4-(1H-pyrazole-4-yl)phenylene-N-(ethyloxamate) [ No CAS ]

Reference： [1]CrystEngComm,2019,vol. 21,p. 2818 - 2831

3
[ 18915-53-2 ]
[ 114474-28-1 ]

Reference： [1]CrystEngComm,2019,vol. 21,p. 2818 - 2831

4
2,4-dichloro-6-isopropoxyquinazoline [ No CAS ]
[ 114474-28-1 ]
N-(4-(1H-pyrazol-4-yl)phenyl)-2-chloro-6-isopropoxyquinazolin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 100.0℃;	To a solution of 2,4-dichloro-6-isopropoxyquinazoline (257 mg, 1.00 mmol) and 4-(4-aminophenyl)pyrazole amine (159 mg, 1.00 mmol) in DMF (2 mL) in a 1-dram vial was added DIEA (258 mg, 2.00 mmol, 0.348 mL). The mixture was heated at 100 C overnight. LC-MS showed one main peak corresponding to the desired product mass. The reaction mixture was cooled to rt and poured into water. The precipitate was filtered and washed with water. The resulting yellow solid was left to dry on the filter overnight to give the title compound (357 mg, 94%), as a yellow solid which was used as is in the next reaction. MS (ES+) m/e 380 (M+H)+.

Reference： [1]Patent: WO2018/201006,2018,A1.Location in patent: Paragraph 0292; 0293

5
2,4-dichloro-6-(2-fluoroethoxy)quinazoline [ No CAS ]
[ 114474-28-1 ]
N-(4-(1H-pyrazol-4-yl)phenyl)-2-chloro-6-(2-fluoroethoxy)quinazolin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 100.0℃;	To a solution of 2,4-dichloro-6-(2-fluoroethoxy)quinazoline (201 mg, 0.77 mmol) and 4-(4-aminophenyl)pyrazole amine (122 mg, 0.77 mmol) in DMF (1.5 mL) in a 1- dram vial was added DIEA (199 mg, 1.54 mmol, 0.268 mL). The vial was flushed with nitrogen and the mixture was heated at 100 C overnight. LC-MS showed one main peak corresponding to the desired product mass. The reaction mixture was cooled to rt and poured into water. The precipitate was filtered and washed with water. The resulting yellow solid was left to dry on the filter for 3 h to give 210 mg, 71%, of a yellow solid which was used as is in the next reaction. MS (ES+) m/e 384 (M+H)+.

Reference： [1]Patent: WO2018/201006,2018,A1.Location in patent: Paragraph 0279; 0280

6
2,4-dichloro-6-propoxyquinazoline [ No CAS ]
[ 114474-28-1 ]
N-(4-(1H-pyrazol-4-yl)phenyl)-2-chloro-6-propoxyquinazolin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 100.0℃;	To a solution of 2,4-dichloro-6-propoxyquinazoline (257 mg, 1.00 mmol) and 4-(4-aminophenyl)pyrazole amine (159 mg, 1.00 mmol) in DMF (2 mL) in a 1-dram vial was added DIEA (258 mg, 2.00 mmol, 0.348 mL). The mixture was heated at 100 C overnight. LC-MS showed one main peak corresponding to the desired product mass. The reaction mixture was cooled to rt and poured into water. The precipitate was filtered and washed with water. The resulting yellow solid was left to dry on the filter for 2 d to give 348 mg, 92%, of crude product which was used as is in the next reaction. MS (ES+) m/e 380/382 (M+H)+.

Reference： [1]Patent: WO2018/201006,2018,A1.Location in patent: Paragraph 0240; 0241

7
2,4-dichloro-6-(2-methoxyethoxy)quinazoline [ No CAS ]
[ 114474-28-1 ]
N-(4-(1H-pyrazol-4-yl)phenyl)-2-chloro-6-(2-methoxyethoxy)quinazolin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 100.0℃;	To a solution of 2,4-dichloro-6-(2-methoxyethoxy)quinazoline (273 mg, 1.00 mmol) and 4-(4-aminophenyl)pyrazole amine (159 mg, 1.00 mmol) in DMF (2 mL) in a 1- dram vial was added DIEA (258 mg, 2.00 mmol, 0.348 mL). The mixture was heated at 100 C overnight. LC-MS showed one main peak corresponding to the desired product mass. The reaction mixture was cooled to rt and poured into water. The precipitate was filtered and washed with water. The resulting yellow solid was left to dry on the filter for 2 h to give 419 mg of crude product which was used as is in the next reaction. MS (ES+) m/e 396/398 (M+H)+.

Reference： [1]Patent: WO2018/201006,2018,A1.Location in patent: Paragraph 0227; 0228

8
[ 174566-15-5 ]
[ 114474-28-1 ]
N-(4-(1H-pyrazol-4-yl)phenyl)-2-chloro-7-fluoroquinazolin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 90℃;	A mixture of 4-(lH-pyrazol-4-yl)aniline (120 mg, 0.75 mmol), 2,4-dichloro- 7-fluoroquinazoline (164 mg, 0.75 mmol), and zPrNEt2 (195 mg, 1.51 mmol) in DMF (2.51 mL) was stirred at 90 C overnight, cooled to rt, diluted with water. The precipitate formed was collected by filtration and washed with water and dried in vacuo to provide the title compound (245 mg, 96%). MS (ES+) m/e 340 (M+H)+.

Reference： [1]Patent: WO2018/201006,2018,A1.Location in patent: Paragraph 0214; 0215

9
[ 134517-57-0 ]
[ 114474-28-1 ]
N-(4-(1H-pyrazol-4-yl)phenyl)-2-chloro-6-fluoroquinazolin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 90.0℃;	A mixture of 4-(lH-pyrazol-4-yl)aniline (120 mg, 0.75 mmol), 2,4-dichloro- 6-fluoroquinazoline (164 mg, 0.75 mmol), and z'Pr Et2 (195 mg, 1.51 mmol) in DMF (2.51 mL) was stirred at 90 C overnight, cooled to rt, diluted with water. The precipitate formed was collected by filtration and washed with water and dried in vacuo to provide the title compound (255 mg, 100%). MS (ES+) m/e 340 (M+H)+.

Reference： [1]Patent: WO2018/201006,2018,A1.Location in patent: Paragraph 0209; 0210

10
[ 114474-28-1 ]
2-(3-(4-((4-(1H-pyrazol-4-yl)phenyl)amino)-7-fluoroquinazolin-2-yl)phenoxy)-N-isopropylacetamide [ No CAS ]

Reference： [1]Patent: WO2018/201006,2018,A1

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Ghs Precautionary Statements

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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.
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.
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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.
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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
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

[ CAS No. 114474-28-1 ]

Quality Control of [ 114474-28-1 ]

Related Doc. of [ 114474-28-1 ]

Product Details of [ 114474-28-1 ]

Computed Properties of [ 114474-28-1 ]

Safety of [ 114474-28-1 ]

Application In Synthesis of [ 114474-28-1 ]

[ 114474-28-1 ] Synthesis Path-Upstream 1~4

[ 114474-28-1 ] Synthesis Path-Downstream 1~10

Related Functional Groups of [ 114474-28-1 ]

Amines

Aryls

Related Parent Nucleus of [ 114474-28-1 ]

Pyrazoles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

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Related Functional Groups of
[ 114474-28-1 ]

Related Parent Nucleus of
[ 114474-28-1 ]