[ CAS No. 25016-16-4 ]

Name: 25016-16-4|1-(1H-Pyrazol-4-yl)ethanone|97%
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Quality Control of [ 25016-16-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 25016-16-4 ]

SDS Specification

Alternatived Products of [ 25016-16-4 ]

Product Details of [ 25016-16-4 ]

CAS No. :	25016-16-4	MDL No. :	MFCD09878739
Formula :	C₅H₆N₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SSGVCJCDGSZFJI-UHFFFAOYSA-N
M.W :	110.11	Pubchem ID :	565593
Synonyms :

Calculated chemistry of [ 25016-16-4 ]

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.2
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	28.78
TPSA :	45.75 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) :	-7.04 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.48
Log Po/w (XLOGP3) :	-0.1
Log Po/w (WLOGP) :	0.61
Log Po/w (MLOGP) :	-0.63
Log Po/w (SILICOS-IT) :	1.26
Consensus Log Po/w :	0.32

Druglikeness

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

Water Solubility

Log S (ESOL) :	-0.86
Solubility :	15.3 mg/ml ; 0.139 mol/l
Class :	Very soluble
Log S (Ali) :	-0.41
Solubility :	43.0 mg/ml ; 0.391 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.51
Solubility :	3.42 mg/ml ; 0.031 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.1

Safety of [ 25016-16-4 ]

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

Application In Synthesis of [ 25016-16-4 ]

* 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 [ 25016-16-4 ]
Downstream synthetic route of [ 25016-16-4 ]

[ 25016-16-4 ] Synthesis Path-Upstream 1~2

1
[ 57121-49-0 ]
[ 25016-16-4 ]

Reference： [1] Monatshefte fuer Chemie, 1988, vol. 119, p. 253 - 262

2
[ 116228-44-5 ]
[ 25016-16-4 ]

Reference： [1] Monatshefte fuer Chemie, 1988, vol. 119, p. 253 - 262

[ 25016-16-4 ] Synthesis Path-Downstream 1~28

1
[ 57121-49-0 ]
[ 25016-16-4 ]

Reference： [1]Monatshefte fur Chemie,1988,vol. 119,p. 253 - 262

3
[ 116228-44-5 ]
[ 25016-16-4 ]

Reference： [1]Monatshefte fur Chemie,1988,vol. 119,p. 253 - 262

4
[ 407-20-5 ]
[ 25016-16-4 ]
1-(1-(5-bromopyridin-3-yl)-1H-pyrazol-4-yl)ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With caesium carbonate; In N,N-dimethyl-formamide; at 120℃; for 0.5h;Microwave irradiation;	A mixture of 3-bromo-5-fluoropyridine (4.1 g, 9.1 mmol), l -(lH-pyrazol-4- yl)ethanone (5, 1.6 g, 9.1 mmol) and Cs2C03(3.55 g, 10.9 mmol) in 15 mL of DMF was heated at 120 C in a microwave oven for 30 minutes. The reaction was cooled to room temperature and diluted with 150 mL of water and filtered. The solid was collected and dried to provide the desired compound (6, 2 g, 7.5 mmol, 83% yield).

Reference： [1]Patent: WO2013/142613,2013,A1 .Location in patent: Page/Page column 122

5
[ 25016-16-4 ]
[ 89466-39-7 ]
1-(1-(6-methoxy-2-methylpyrimidin-4-yl)-1H-pyrazol-4-yl)ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In N,N-dimethyl-formamide; at 20 - 70℃; for 4h;	To a solution of 4-chloro-6-methoxy-2-methylpyrimidine (1.60 g, 10.1 mmol) and l -(H- pyrazol-4-yl)ethanone (1.11 g, 10.1 mmol) in DMF (15.0 mL) was added Cs2C03 (9.86 g, 30.2 mmol) at RT. The reaction solution was stirred at 70 C for 4 h. The resulting mixture was diluted with brine (60 mL) and extracted with ethyl acetate (3 x 60 mL). The combined organic extracts were dried with anhydrous Na2SC>4 and filtered. The filtrate was concentrated under reduced pressure. The crude title compound was obtained as a solid and used in the next step without further purification. MS = 233.1 (M+l).

Reference： [1]Patent: WO2016/154081,2016,A1 .Location in patent: Page/Page column 51-52

6
(1R,4R)-N1-(5-chloro-4-(5-(cyclopropylmethyl)-1-methyl-1H-pyrazol-4-yl)pyrimidin-2-yl)cyclohexane-1,4-diamine hydrochloride [ No CAS ]
[ 25016-16-4 ]
(1R,4R)-N1-(1(1H-pyrazol-4-yl)ethyl)-N4-(5-chloro-4-(5-(cyclopropylmethyl)-1-methyl-1H-pyrazol-4-yl)pyrimidin-2-yl)cyclohexane-1,4-diamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
17.5%		Preparation of (lRAR^-d-dH-pyrazol^-yDethyD-N S-chloro^S- (cyclopropylmethyl)-l-methyl-lH-pyrazol-4-yl)pyrimidin-2-yl)cyclohexane-lA- diamine (A83) To a solution of A-51(100.00 mg, 251.67 mupiiotaomicron, 1.00 eq, HQ), compound 83_1 (27.71 mg, 251.67 mupiiotaomicron, 1.00 eq) were added TEA (503.34 mupiiotaomicron, 69.77 uL, 2.00 eq) and 02429524H5-01 Ti(i-PrO)4 (149 muL·, 503.34 muetaiotaomicron, 2.00 eq). The mixture was stirred at 80 C for 12 hours. Then NaBCN (39.54 mg, 629.18 mupiiotaomicron, 2.50 eq) was added. The resulting mixture was stirred at 15 C for 4 hours. The mixture was quenched with a.q NaHCCb (50 mL) and extracted with DCM (50 mL*2). The organic layer was concentrated and purified by prep- HPLC (basic condition) to give A-83 (20.00 mg, 43.96 mupiiotaomicron, 17.5% yield) as a yellow solid. LCMS: RT = 1.897 m/z 455.2[M+H]+ NMR (CDCb, 400 MHz) S 8.19 (s, 1H), 8.12 (s, 1H), 7.52 (s, 2H), 4.90 (d, /=7.6Hz, 1H), 4.05-4.00 (m, 1H), 3.91 (s, 3H), 3.78-3.76 (m, 1H), 3.06 (d, /=5.6Hz, 2H), 2.49-2.46 (m, 1H), 2.11-2.08 (m, 4H), 1.40-1.38 (m, 3H), 1.25-1.19(m, 4H), 1.05 (s, 1H), 0.47-0.44 (m, 2H), 0.16-0.15 (m, 2H).

Reference： [1]Patent: WO2017/21969,2017,A1 .Location in patent: Page/Page column 78-79

7
[ 25016-16-4 ]
[ 206193-17-1 ]
(S)-3-(4-acetyl-1H-pyrazol-1-yl)-N-(4-cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-2-methylpropanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
20%		(5)-3-(4-Acetyl- lH-pyrazol- l-yl)-N-(4-cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-2- methylpropanamide (Ci7Hi5F3 (0857) [00394] To a solution of l-(lH-pyrazol-4-yl)ethanone (0.10 g, 0.000908 mol) in anhydrous THF (5 mL), which was cooled in an ice water bath under an argon atmosphere, was added sodium hydride (60% dispersion in oil, 0.11 g, 0.002725 mol). After addition, the resulting mixture was stirred for 3 h. ( ?)-3-Bromo-N-(4-cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-2-methylpropanamide (8, 0.32 g, 0.000908 mol) was added to the above solution, and the resulting reaction mixture was allowed to stir overnight at RT under argon. The reaction was quenched by water, and extracted with ethyl acetate. The organic layer was washed with brine, dried with MgS04, filtered, and concentrated under vacuum. The product was purified by a silica gel column using DCM and ethyl acetate (19: 1) as eluent to afford 70 mg (20%) of the titled compound as yellowish solid. (0858) [00395] Compound 1035 was characterized as follows: NMR (400 MHz, DMSO-i delta 10.37 (s, 1H, NH), 8.45 (d, = 1.2 Hz, 1H, ArH), 8.25 (s, 1H, Pyrazole-H), 8.23 (d, = 8.2 Hz, = 1.2 Hz, 1H, ArH), 8.10 (d, = 8.2 Hz, 1H, ArH), 7.86 (s, 1H, Pyrazole-H), 6.37 (s, 1H, OH), 4.50 (d, = 14.0 Hz, 1H, CH), 4.33 (d, = 14.0 Hz, 1H, CH), 2.34 (s, 3H, CH3), 1.39 (s, 3H, CH3); mass (ESI, Negative): 379.14 [M-H]-; (ESI, Positive): 413.18 [M+Na]+.

Reference： [1]Patent: WO2017/214634,2017,A1 .Location in patent: Paragraph 00394-00395

8
2-chloro-N-[(dimethylamino)methylene]-5-nitrobenzenesulfonamide [ No CAS ]
[ 4637-24-5 ]
[ 25016-16-4 ]
N-[(dimethylamino)methylene]-2-(3-formyl-1H-pyrazol-1-yl)-5-nitrobenzenesulfonamide [ No CAS ]