[ CAS No. 97421-13-1 ] {[proInfo.proName]}

Name: 97421-13-1|1-(tert-Butyl)-1H-pyrazol-4-amine|98%
Brand: Ambeed
SKU: A120370
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Quality Control of [ 97421-13-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 97421-13-1 ]

SDS Specification

Alternatived Products of [ 97421-13-1 ]

Product Details of [ 97421-13-1 ]

CAS No. :	97421-13-1	MDL No. :	MFCD11845713
Formula :	C₇H₁₃N₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JPUFJDDEDJUDHE-UHFFFAOYSA-N
M.W :	139.20	Pubchem ID :	13469817
Synonyms :

Calculated chemistry of [ 97421-13-1 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.57
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	42.2
TPSA :	43.84 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.84 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.51
Log Po/w (XLOGP3) :	0.44
Log Po/w (WLOGP) :	1.23
Log Po/w (MLOGP) :	0.46
Log Po/w (SILICOS-IT) :	0.2
Consensus Log Po/w :	0.77

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.28
Solubility :	7.23 mg/ml ; 0.052 mol/l
Class :	Very soluble
Log S (Ali) :	-0.93
Solubility :	16.4 mg/ml ; 0.118 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.23
Solubility :	8.14 mg/ml ; 0.0585 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.53

Safety of [ 97421-13-1 ]

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 [ 97421-13-1 ]

* 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 [ 97421-13-1 ]
Downstream synthetic route of [ 97421-13-1 ]

[ 97421-13-1 ] Synthesis Path-Upstream 1~1

1
[ 97421-12-0 ]
[ 97421-13-1 ]

Yield	Reaction Conditions	Operation in experiment
92%	With hydrogen In methanol at 20℃; for 3 h;	To a solution of l-tert-butyl-4-nitro-lH-pyrazole (1.10 g, ^" 6.5 mmol) in methanol (20 mL) was added 10percent palladium carbon (containing 50percent water, 442 rug) , and the mixture was stirred under a hydrogen atmosphere at room temperature for 3 hr. The catalyst was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, hexane/ethyl acetate=70/30->0/100) to give the title compound (838 mg, 92percent) . ¹H-NMR (CDCl₃, 300 MHz) δ 1-53 (9H, s) , 2.86 (2H, br s) , 7.15(IH, s) , 7.19 (IH, s) .

Reference： [1] Patent: WO2007/4749, 2007, A1, . Location in patent: Page/Page column 155
[2] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 20, p. 7150 - 7163
[3] Patent: WO2012/61337, 2012, A1, . Location in patent: Page/Page column 48
[4] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 2, p. 145 - 151

[ 97421-13-1 ] Synthesis Path-Downstream 1~24

1
[ 97421-12-0 ]
[ 97421-13-1 ]

Yield	Reaction Conditions	Operation in experiment
92%	With hydrogen;palladium 10% on activated carbon; In methanol; at 20℃; for 3.0h;	To a solution of l-tert-butyl-4-nitro-lH-pyrazole (1.10 g, " 6.5 mmol) in methanol (20 mL) was added 10% palladium carbon (containing 50% water, 442 rug) , and the mixture was stirred under a hydrogen atmosphere at room temperature for 3 hr. The catalyst was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, hexane/ethyl acetate=70/30->0/100) to give the title compound (838 mg, 92%) . 1H-NMR (CDCl3, 300 MHz) delta 1-53 (9H, s) , 2.86 (2H, br s) , 7.15(IH, s) , 7.19 (IH, s) .
	With hydrogen;palladium 10% on activated carbon; In methanol; for 1.0h;	To a solution of 4-nitro- IH-pyrazole which was prepared as described in J. Med Chem. 2005, 48, 5780 (0.5 g, 4.4 mmol) in dioxane (8 mL) was added tert-butylacetate (3 mL) and cone. Iota¾804 (0.26 mL) and the mixture was stirred for 18 h at room temperature. The reaction mixture was diluted with sat. NaHC03, volatiles were evaporated and mixture was extracted with ethyl acetate. The organic phase was dried (MgS04), filtered and evaporated to afford a crude residue which was purified bychromatography on silica gel (CH2CI2). Isolated l-tert-butyl-4-nitro-lH-pyrazole (250 mg): 1H NMR (400 MHz, DMSO-d6) delta 8.24 (s, 1H), 8.09 (s, 1H), 1.63 (s, 9H). To a solution 1- tert-butyl-4-nitro-lH-pyrazole (250 mg, 1.5 mmol) in methanol (10 mL) was added 10% Pd/C (80 mg) and the mixture was stirred under hydrogen for lh. The reaction was filtered and the filtrate was evaporated to afford l-tert-butyl-lH-pyrazol-4-amine which was used directly without any further purification.

Reference： [1]Patent: WO2007/4749,2007,A1 .Location in patent: Page/Page column 155
[2]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 7150 - 7163
[3]Patent: WO2012/61337,2012,A1 .Location in patent: Page/Page column 48
[4]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 145 - 151

2
[ 97421-13-1 ]
[ 919278-09-4 ]
[ 32315-10-9 ]
1-(1-tert-butyl-1H-pyrazol-4-yl)-3-{2-chloro-4-[(5-methyl-5H-pyrrolo[3,2-d]pyrimidin-4-yl)oxy]phenyl}urea [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 7150 - 7163

3
[ 97421-13-1 ]
[ 1188910-66-8 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 1082 - 1105

4
[ 97421-13-1 ]
[ 1188910-65-7 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 1082 - 1105

5
[ 97421-13-1 ]
[ 1885-14-9 ]
[ 857266-91-2 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 1082 - 1105

6
[ 97421-13-1 ]
3-(trans-2-((tert-butoxycarbonyl)amino)cyclopropyl)benzoic acid [ No CAS ]
tert-butyl (trans-2-(3-((1-(tert-butyl)-1H-pyrazol-4-yl)carbamoyl)phenyl)cyclopropyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
776 mg	With triethylamine; HATU; In water; N,N-dimethyl-formamide; at 0 - 20℃; for 48.0h;	A) tert-butyl (trans-2-(3-((1-(tert-butyl)-1H-pyrazol-4-yl)carbamoyl)phenyl)cyclopropyl)carbamate 3-(trans-2-((tert-Butoxycarbonyl)amino)cyclopropyl)benzoic acid (670 mg), <strong>[97421-13-1]1-(tert-butyl)-1H-pyrazol-4-amine</strong> (460 mg) and triethylamine (1.35 mL) were dissolved in anhydrous DMF (15.0 mL), and the mixture was cooled to 0 C. O-(7-Azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate (1.84 g) was added, and the mixture was stirred at room temperature for 2 days. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extracts were combined, washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous sodium sulfate. The solution was purified by short silica gel column chromatography (ethyl acetate), purified by NH silica gel column chromatography (ethyl acetate) and concentrated under reduced pressure. The obtained residue was washed with diisopropy ether under insonation to give the title compound (776 mg). MS (API+): [M+H]+ 399.4.

Reference： [1]Patent: US2015/266881,2015,A1 .Location in patent: Paragraph 1095; 1096

7
[ 97421-13-1 ]
(3R,4S)-tert-butyl 4-(4-(4-((1-(tert-butyl)-1H-pyrazol-4-yl)amino)-1,3,5-triazin-2-yl)-2-cyanophenoxy)-3-fluoropiperidine-1-carboxylate [ No CAS ]

Reference： [1]Patent: US2016/96827,2016,A1

8
[ 97421-13-1 ]
5-(4-((1-(tert-butyl)-1H-pyrazol-4-yl)amino)-1,3,5-triazin-2-yl)-2-(((3R,4S)-3-fluoropiperidin-4-yl)oxy)benzonitrile [ No CAS ]

Reference： [1]Patent: US2016/96827,2016,A1

9
[ 97421-13-1 ]
5-(4-((1-(tert-butyl)-1H-pyrazol-4-yl)amino)-1,3,5-triazin-2-yl)-2-(((3R,4S)-3-fluoro-1-((S)-2-hydroxypropanoyl)piperidin-4-yl)oxy)benzonitrile [ No CAS ]

Reference： [1]Patent: US2016/96827,2016,A1

10
[ 2831-66-5 ]
[ 97421-13-1 ]
N-(1-(tert-butyl)-1H-pyrazol-4-yl)-4-chloro-1,3,5-triazin-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 0℃;	To a solution of 2,4- dichloro-i,3,5-triazine (1.2 g, 7.9 mmol) in N,N-dimethylformamide (DMF, 10 mE) at 0 C. were added sequentially N,N-diisopropylethylamine (DIEA, 1.4 mE, 8.3 mmol) and a solution of 1 -(tert-butyl)-i H-pyrazol-4-amine (Matrix Scientific, 1.0 g, 7.2 mmol) in DMF (15 mE). The mixture was allowed to warm to room temperature. The mixture was diluted with ethyl acetate and water. The aqueous phase basified with saturated aqueous sodium hydrogen carbonate solution and then was extracted thrice with ethyl acetate. The combined extracts were dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel) to provide N-(i -(tert-butyl)-i H-pyrazol-4-yl)-4-chioro-i ,3, 5-triazin-2-amine. ECMS-ESI (mlz): [M+H] calcd for C,0H,4C1N5: 253.1. found: 252.9

Reference： [1]Patent: US2016/96827,2016,A1 .Location in patent: Paragraph 1034

11
[ 97421-13-1 ]
C₃₂H₃₂FN₇O₃ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 145 - 151

12
[ 97421-13-1 ]
C₃₀H₃₀FN₇O₂ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 145 - 151

13
[ 10132-07-7 ]
[ 97421-13-1 ]
C₁₁H₁₅ClN₆ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 145 - 151

14
[ 97421-13-1 ]
1-(tert-butyl)-5-(p-tolyl)-1-pyrazolo[4,3-b]pyridine [ No CAS ]