[ CAS No. 114474-28-1 ]

Name: 114474-28-1|4-(1H-Pyrazol-4-yl)aniline|97%
Brand: Ambeed
SKU: A105393
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Quality Control of [ 114474-28-1 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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 :	NIIAGRDJQKKSKU-UHFFFAOYSA-N
M.W :	159.19 g/mol	Pubchem ID :	13977013
Synonyms :

Calculated chemistry of [ 114474-28-1 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	11
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	2.0
Molar Refractivity :	48.43
TPSA :	54.7 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) :	-6.45 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.84
Log Po/w (XLOGP3) :	1.16
Log Po/w (WLOGP) :	1.67
Log Po/w (MLOGP) :	0.85
Log Po/w (SILICOS-IT) :	1.86
Consensus Log Po/w :	1.28

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.17
Solubility :	1.08 mg/ml ; 0.00676 mol/l
Class :	Soluble
Log S (Ali) :	-1.9
Solubility :	1.99 mg/ml ; 0.0125 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-3.38
Solubility :	0.0662 mg/ml ; 0.000416 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.39

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 ]

* 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 [ 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 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 1~59

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

Yield	Reaction Conditions	Operation in experiment
94%	With palladium 10% on activated carbon; hydrogen; at 20.0℃;	To a suspension of 4-(4-Nitrophenyl)-1H-pyrazole (8.3 g, 43.88 mmol) in MeOH/DME (2:1 v/v) was added 10% 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 (94%) of a yellow solid. ?H NIVIR (400 MHz, DMSO-d6) oe 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 20.0℃; under 1838.94 Torr; for 2.0h;	[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 10% 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 (94%) of a yellow solid. 1H NMR (400 MHz, DMSO-d6) delta 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)+.
	With hydrogen;	Intermediate 259 corresponds with CAS: 114474-26-9. Hydrogenation of the nitro group according to wellk-known methods afforded intermediate 260.

90 mg

With palladium 10% on activated carbon; hydrogen; In methanol; at 20.0℃; for 4.0h;

A mixture containing 4-(4-nitrophenyl)-1H-pyrazole (commercially available from Combi-Blocks, 110 mg), 10% Pd/C (11 mg)and methanol (5 mL) was stirred at room temperature for 4 hours under a hydrogen atmosphere. Insoluble substances in the reaction mixture were filtered off. Then, the filtrate was concentrated under a reduced pressure, and thereby 4-(1H-pyrazol-4-yl)aniline (90 mg)as a brown solid was obtained.

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]CrystEngComm,2019,vol. 21,p. 2818 - 2831
[4]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1987,vol. 26,p. 616 - 619
[5]Patent: WO2019/120209,2019,A1 .Location in patent: Page/Page column 216
[6]Patent: US2019/337926,2019,A1 .Location in patent: Paragraph 0692

2
[ 104-03-0 ]
PbO [ No CAS ]
[ 114474-28-1 ]

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

3
[ 93072-94-7 ]
[ 114474-28-1 ]

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

4
[ 114474-28-1 ]
[ 114474-32-7 ]

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

5
[ 1643545-71-4 ]
[ 114474-28-1 ]
[ 1181326-94-2 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 3856 - 3873

6
[ 114474-28-1 ]
2-(3-(4-((4-(1H-pyrazol-4-yl)phenyl)amino)-5,7-dihydrofuro[3,4-d]pyrimidin-2-yl)phenoxy)-N-isopropylacetamide [ No CAS ]

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

7
[ 114474-28-1 ]
C₂₆H₂₄N₆O₃ [ No CAS ]

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

8
[ 114474-28-1 ]
C₂₇H₂₆N₆O₃ [ No CAS ]

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

9
[ 114474-28-1 ]
C₂₈H₂₈N₆O₃ [ No CAS ]

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

10
[ 114474-28-1 ]
2-(3-(4-((4-(1H-pyrazol-4-yl)phenyl)amino)-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-6-yl)phenoxy)-N-cyclobutylacetamide [ No CAS ]

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

11
[ 114474-28-1 ]
2-(3-(4-((4-(1H-pyrazol-4-yl)phenyl)amino)-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-6-yl)phenoxy)-N-isopropylacetamide [ No CAS ]

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

12
[ 114474-28-1 ]
2-(3-(4-((4-(1H-pyrazol-4-yl)phenyl)amino)-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-6-yl)phenoxy)-N-cyclopentylacetamide [ No CAS ]

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

13
[ 114474-28-1 ]
2-(3-(4-((4-(1H-pyrazol-4-yl)phenyl)amino)-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-6-yl)phenoxy)-N-isobutylacetamide [ No CAS ]

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

14
[ 114474-28-1 ]
2-(3-(4-((4-(1H-pyrazol-4-yl)phenyl)amino)pyrido[3,4-d]pyrimidin-2-yl)phenoxy)-N-isopropylacetamide [ No CAS ]

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

15
[ 114474-28-1 ]
2-(3-(4-((4-(1H-pyrazol-4-yl)phenyl)amino)pyrido[3,4-d]pyrimidin-2-yl)phenoxy)-N-cyclobutylacetamide [ No CAS ]

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

16
[ 114474-28-1 ]
2-(3-(4-((4-(1H-pyrazol-4-yl)phenyl)amino)pyrido[3,4-d]pyrimidin-2-yl)phenoxy)-N-cyclopentylacetamide [ No CAS ]

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

17
[ 114474-28-1 ]
2-(3-(7-((4-(1H-pyrazol-4-yl)phenyl)amino)thiazolo[5,4-d]pyrimidin-5-yl)phenoxy)-N-isopropylacetamide [ No CAS ]

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

18
[ 114474-28-1 ]
2-(3-(7-((4-(1H-pyrazol-4-yl)phenyl)amino)thiazolo[5,4-d]pyrimidin-5-yl)phenoxy)-N-cyclobutylacetamide [ No CAS ]

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

19
[ 114474-28-1 ]
2-(3-(7-((4-(1H-pyrazol-4-yl)phenyl)amino)thiazolo[5,4-d]pyrimidin-5-yl)phenoxy)-N-cyclopentylacetamide [ No CAS ]

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

20
[ 114474-28-1 ]
2-(3-(7-((4-(1H-pyrazol-4-yl)phenyl)amino)thiazolo[5,4-d]pyrimidin-5-yl)phenoxy)-N-isobutylacetamide [ No CAS ]

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

21
[ 98141-42-5 ]
[ 114474-28-1 ]
N-(4-(1H-pyrazol-4-yl)phenyl)-6-chloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 100℃; for 5h;	A mixture of 4,6-dichloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidine (300 mg, 1.50 mmol), <strong>[114474-28-1]4-(1H-pyrazol-4-yl)aniline</strong> (235, 1.50 mmol), and iPr2NEt (0.52 mL, 0.74 mmol) in DIVIF (3.0 mL) was heated at 100 C for 5h, cooled to rt, and diluted with water. The precipitate formed was collected by filtration and washed with water and dried in vacuo to provide the title compound (470 mg, 98%). ?H NIVIR (400 MHz, DMSO-d6) oe 12.95 (s, 1H), 10.48 (s, 1H), 8.26 (d, J 61.6 Hz, 2H), 7.95 (s, 1H), 7.84-7.51 (m, 4H), 3.91 (s, 3H). MS (ES+) m/e 326 (M+H).
98%	With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 100℃; for 5h;	[0233] A mixture of 4,6-dichloro-l-methyl-lH-pyrazolo[3,4-d]pyrimidine (300 mg, 1.50 mmol), 4-(lH-pyrazol-4-yl)aniline (235, 1.50 mmol), and iPr2NEt (0.52 mL, 0.74 mmol) in DMF (3.0 mL) was heated at 100 C for 5h, cooled to rt, and diluted with water. The precipitate formed was collected by filtration and washed with water and dried in vacuo to provide the title compound (470 mg, 98%). 1H NMR (400 MHz, DMSO-i/6) delta 12.95 (s, 1H), 10.48 (s, 1H), 8.26 (d, J= 61.6 Hz, 2H), 7.95 (s, 1H), 7.84 - 7.51 (m, 4H), 3.91 (s, 3H). MS (ES+) m/e 326 (M+H)+.

Reference： [1]Patent: WO2016/210331,2016,A1 .Location in patent: Paragraph 0114; 115
[2]Patent: WO2016/210330,2016,A1 .Location in patent: Paragraph 0232-0233

22
[ 908240-50-6 ]
[ 114474-28-1 ]
N-(4-(1H-pyrazol-4-yl)phenyl)-2-chloropyrido[3,4-d]pyrimidin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 100℃; for 5h;	A mixture of 2,4-dichloropyrido[3,4-d]pyrimidine (250 mg, 1.25 mmol), 4-(1H- pyrazol-4-yl)aniline (199, 1.25 mmol), and iPr2NEt (0.44 mL, 2.50 mmol) in DIVIF (2.5 mL) was heated at 100 C for 5h, cooled to rt, and diluted with water. The precipitate formed was collected by filtration and washed with water and dried in vacuo to provide the title compound (400 mg,99%). MS 19S+) m/e 323 (M+H) .
99%	With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 100℃; for 5h;	[0255] A mixture of 2,4-dichloropyrido[3,4-d]pyrimidine (250 mg, 1.25 mmol), 4-(lH- pyrazol-4-yl)aniline (199, 1.25 mmol), and iPr2NEt (0.44 mL, 2.50 mmol) in DMF (2.5 mL) was heated at 100 C for 5h, cooled to rt, and diluted with water. The precipitate formed was collected by filtration and washed with water and dried in vacuo to provide the title compound (400 mg, 99%). MS (ES+) m/e 323 (M+H) +.

Reference： [1]Patent: WO2016/210331,2016,A1 .Location in patent: Paragraph 0125; 0126
[2]Patent: WO2016/210330,2016,A1 .Location in patent: Paragraph 0254-0255

23
[ 13479-88-4 ]
[ 114474-28-1 ]
N-(4-(1H-pyrazol-4-yl)phenyl)-5-chlorothiazolo[5,4-d]pyrimidin-7-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 100℃; for 5.0h;	A mixture of 5,7-dichlorothiazolo[5,4-d]pyrimidine (300 mg, 1.46 mmol), 4-(1H- pyrazol-4-yl)aniline (233, 1.46 mmol), and iPr2NEt (0.51 mL, 2.93 mmol) in DIVIF (2.9 mL) was heated at 100 C for 5h, cooled to rt, and diluted with water. The precipitate formed was collected by filtration and washed with water and dried in vacuo to provide the title compound (470 mg, 98%). MS (ES+) m/e 329 (M+H).
98%	With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 100℃; for 5.0h;	[0264] A mixture of 5,7-dichlorothiazolo[5,4-d]pyrimidine (300 mg, 1.46 mmol), 4-(lH- pyrazol-4-yl)aniline (233, 1.46 mmol), and iPr2NEt (0.51 mL, 2.93 mmol) in DMF (2.9 mL) was heated at 100 C for 5h, cooled to rt, and diluted with water. The precipitate formed was collected by filtration and washed with water and dried in vacuo to provide the title compound (470 mg, 98%). MS (ES+) m/e 329 (M+H)+.

Reference： [1]Patent: WO2016/210331,2016,A1 .Location in patent: Paragraph 0134; 0135
[2]Patent: WO2016/210330,2016,A1 .Location in patent: Paragraph 0263-0264

24
[ 104-03-0 ]
[ 114474-28-1 ]

Reference： [1]Patent: WO2016/210331,2016,A1
[2]Patent: WO2016/210330,2016,A1
[3]CrystEngComm,2019,vol. 21,p. 2818 - 2831

25
[ 676605-99-5 ]
[ 114474-28-1 ]

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

26
[ 39551-54-7 ]
[ 114474-28-1 ]
N-(4-(1H-pyrazol-4-yl)phenyl)-2-chloropyrido[3,2-d]pyrimidin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 100.0℃; for 5.0h;	[0210] A mixture of 2,4-dichloropyrido[3,2-d]pyrimidine (300 mg, 1.50 mmol), 4-(lH- pyrazol-4-yl)aniline (239, 1.50 mmol), and iPr2NEt (0.52 mL, 0.74 mmol) in DMF (3.0 mL) was heated at 100 C for 5h, cooled to rt, and diluted with water. The precipitate formed was collected by filtration and washed with water and dried in vacuo to provide the title compound (480 mg, 99%). MS (ES+) m/e 323 (M+H)+.

Reference： [1]Patent: WO2016/210330,2016,A1 .Location in patent: Paragraph 0209-0210

27
[ 939979-32-5 ]
[ 114474-28-1 ]
N-(4-(1H-pyrazol-4-yl)phenyl)-5-chloro-1-methyl-1H-pyrazolo[4,3-d]pyrimidin-7-amine [ No CAS ]