137890-05-2|1-(1-Methyl-1H-pyrazol-5-yl)ethanone| Ambeed

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Quality Control of [ 137890-05-2 ] Purity: 95% SDS Specification

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Product Details of [ 137890-05-2 ]

CAS No. :	137890-05-2
Formula :	C₆H₈N₂O
M.W :	124.14
SMILES Code :	CN1N=CC=C1C(C)=O
MDL No. :	MFCD04968784
InChI Key :	UXNMMULCZUAIHE-UHFFFAOYSA-N
Pubchem ID :	7017416

Safety of [ 137890-05-2 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Computational Chemistry of [ 137890-05-2 ] Show Less

Physicochemical Properties

Num. heavy atoms	9
Num. arom. heavy atoms	5
Fraction Csp3	0.33
Num. rotatable bonds	1
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	33.68
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	34.89 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.38
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	0.25
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.62
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	-0.25
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	0.61
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.52

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.11
Solubility	9.59 mg/ml ; 0.0772 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-0.54
Solubility	35.5 mg/ml ; 0.286 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-1.09
Solubility	10.1 mg/ml ; 0.0815 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.88 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.3

Application In Synthesis of [ 137890-05-2 ]

* 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 [ 137890-05-2 ]

[ 137890-05-2 ] Synthesis Path-Downstream 1~23

1
[ 137890-05-2 ]
[ 137890-09-6 ]

References: [1]Chemistry of Heterocyclic Compounds,1991,vol. 27,p. 656 - 658.
Khimiya Geterotsiklicheskikh Soedinenii,1991,vol. 27,p. 833 - 835.

2
[ 66121-72-0 ]
[ 74-88-4 ]
[ 137890-05-2 ]

References: [1]Chemistry of Heterocyclic Compounds,1991,vol. 27,p. 656 - 658.
Khimiya Geterotsiklicheskikh Soedinenii,1991,vol. 27,p. 833 - 835.

3
[ 137890-05-2 ]
2-methyl-2H-pyrazole-3-carboxylic acid ethyl ester [ No CAS ]
[ 1006328-59-1 ]

References: [1]Chemistry of Heterocyclic Compounds,2011,vol. 47,p. 695 - 699.

4
[ 16034-46-1 ]
[ 137890-05-2 ]

References: [1]Journal of Heterocyclic Chemistry,2012,vol. 49,p. 1422 - 1424.
[2]Patent: WO2018/160878,2018,A1 .

5
[ 84547-59-1 ]
[ 137890-05-2 ]

References: [1]Journal of Heterocyclic Chemistry,2012,vol. 49,p. 1422 - 1424.

6
C₁₂H₁₆N₂O₅ [ No CAS ]
[ 137890-05-2 ]

References: [1]Journal of Heterocyclic Chemistry,2012,vol. 49,p. 1422 - 1424.

Yield	Reaction Conditions	Operation in experiment
570 mg		General procedure: A solution of 580 mg (3.15 mmol) of N-methoxy-N-methyl-3,5-dimethylisoxazole-4-carboxamide in 20 mL of THF is cooled to 0C. A solution of 1.57 mL (4.72 mmol) of 3 M methylmagnesium bromide in ether is added. After stirring for 4 hours at room temperature, the reaction medium is taken up in 10 mL of 1 N HCl and stirred for a further 1 hour at room temperature. The mixture is then basified with K2CO3 and extracted with ethyl acetate. The organic phase is dried over magnesium sulfate and evaporated to dryness to give 420 mg of 1-(3,5-dimethylisoxazol-4-yl)ethanone, corresponding to the following characteristics: LC/MS (method G): [M+H]+: m/z 140 tr (min) = 1.06. 1H NMR spectrum (300 MHz, delta in ppm, CDCl3): 2.48 (s, 6H), 2.70 (s, 3H).
570 mg	In tetrahydrofuran; at 0 - 20℃; for 4h;	General procedure: A solution of 580 mg (3.15 mmol) of N-methoxy-N-methyl-3,5-dimethylisoxazole-4-carboxamide in 20 mL of THF is cooled to 0 C. A solution of 1.57 mL (4.72 mmol) of 3 M methylmagnesium bromide in ether is added. After stirring for 4 hours at room temperature, the reaction medium is taken up in 10 mL of 1 N HCl and stirred for a further 1 hour at room temperature. The mixture is then basified with K2CO3 and extracted with ethyl acetate. The organic phase is dried over magnesium sulfate and evaporated to dryness to give 420 mg of 1-(3,5-dimethylisoxazol-4-yl)ethanone, corresponding to the following characteristics: LC/MS (method G): [M+H]+: m/z 140 tr (min)=1.06 1H NMR spectrum (300 MHz, delta in ppm, CDCl3): 2.48 (s, 6H), 2.70 (s, 3H).

8
[ 137890-05-2 ]
[ 1616100-88-9 ]

References: [1]Patent: WO2014/98831,2014,A1 .

9
[ 137890-05-2 ]
(1R,3S)-3-amino-3-(2,4-difluorophenyl)-1-(1-methyl-1H-pyrazol-5-yl)butan-1-ol hydrochloride [ No CAS ]

References: [1]Patent: WO2014/98831,2014,A1 .

10
[ 137890-05-2 ]
[ 1616100-90-3 ]

References: [1]Patent: WO2014/98831,2014,A1 .

11
[ 137890-05-2 ]
(4S,6S)-4-(2,4-difluorophenyl)-4-methyl-6-(1-methyl-1H-pyrazol-5-yl)-5,6-dihydro-4H-1,3-thiazin-2-amine trifluoroacetate [ No CAS ]

References: [1]Patent: WO2014/98831,2014,A1 .

12
[ 1585971-57-8 ]
[ 137890-05-2 ]
[ 1616100-87-8 ]

Yield	Reaction Conditions	Operation in experiment
27%		Preparation 74 (R)-N-((5)-2-(2,4-difluorophenyl)-4-(l -methyl- lH-pyrazol-5-yl)-4-oxobutan-2-yl)-2- methylpropane-2-sulfinamide A solution of 2.4 M n-butyllithium in hexane (1.933 mL, 4.83 mmol) was added to a solution of 1-(1 -methyl- lH-pyrazol-5-yl)ethanone (600 mg, 4.83 mmol) in THF (20 mL) maintained at -78 C under a nitrogen atmosphere. The resulting mixture was allowed to stir for 20 min at -78 C. A solution of (R,E)-N-(l-(2,4-difluorophenyl)ethylidene)-2- methylpropane-2-sulfinamide (preparation 73, 836 mg, 3.22 mmol) in THF (5 mL) was slowly added over 2 min. After 5 min, the resulting solution was warmed to between -30 and -20 C and allowed to stir for 24 h. The reaction was quenched with saturated aqueous ammonium chloride solution and extracted with EtOAc. The combined organics were washed with brine, dried over magnesium sulfate, and filtered. The filtrate was concentrated in vacuo. The crude product was purified using silica gel column chromatography (5: 1-1 : 1 hexanes/ethyl acetate, linear gradient) to afford ( ?)-N-((5)-2- (2,4-difluorophenyl)-4-(l -methyl- lH-pyrazol-5-yl)-4-oxobutan-2-yl)-2-methylpropane-2- sulfinamide (330 mg, 0.861 mmol, 27 % yield). MS (M+Na)+: 406.1.

References: [1]Patent: WO2014/98831,2014,A1 .Location in patent: Page/Page column 73; 74.

13
[ 20583-33-9 ]
[ 74-88-4 ]
[ 137890-04-1 ]
[ 137890-05-2 ]

Yield	Reaction Conditions	Operation in experiment
58%; 13%	With potassium carbonate; In acetonitrile; at 20℃; for 72h;	Preparation 72 1-(1 -methyl- lH-pyrazol-5-yl)ethanone Iodomethane (4.68 mL, 74.8 mmol) was added to a stirred mixture of l-(lH-pyrazol-5- yl)ethanone (8.24g, 74.8 mmol) and potassium carbonate (20.58 g, 149 mmol) in acetonitrile (50 mL). The mixture was left to stir at rt for 3 days. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The crude product was purified using silica gel column chromatography (5: 1-2: 1 hexane/ethyl acetate, linear gradient) to afford 1 -(1 -methyl- 1H- pyrazol-5-yl)ethanone (1.20 g, 9.67 mmol, 13 % yield) (less polar component, first to elute) and 1-(1 -methyl- lH-pyrazol-3-yl)ethanone (5.40 g, 43.5 mmol, 58 % yield) (more polar component, second to elute). Data for 1-(1 -methyl- lH-pyrazol-5-yl)ethanone : XH NMR (500MHz, CHLOROFORM-d) delta 7.47 (d, J=2.0 Hz, 1H), 6.83 (d, J=2.1 Hz, 1H), 4.17 (s, 3H), 2.52 (s, 3H). MS (M+H)+: 125.2. Data for 1-(1 -methyl- lH-pyrazol-3- yl)ethanone: NMR (500MHz, chloroform-d) delta 7.38 (d, J=2.3 Hz, 1H), 6.78 (d, J=2.4 Hz, 1H), 3.98 (s, 3H), 2.57 (s, 3H). MS (M+H)+: 125.2.

References: [1]Patent: WO2014/98831,2014,A1 .Location in patent: Page/Page column 72.

14
C₁₄H₁₅F₃N₄S*(x)C₂HF₃O₂ [ No CAS ]
[ 137890-05-2 ]
C₂₀H₂₃F₃N₆S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
104 mg		Under N2, a mixture of intermediate 1 lb (1 g) and 5-acetyl-l-methylpyrazole (168mgl.35 mmol) in THF (15 mL) was stirred at rt overnight. Then, NaBH(OAc)3 (718 mg;3.4 mmol) was added portion wise. The reaction mixture was stirred at room temperature for 72h, poured into cold water, basified with K2C03 powder and extracted with EtOAc. The organic layer was dried over MgSO4, filtered and evaporated to dryness. The residue was purified by chromatography over silica gel (irregular SiOH, 12g; mobile phase:gradient from 100% DCM, 0% MeOH to 95% DCM, 5% MeOH, 0.3% NH4OH). The fractions were collected and evaporated to dryness. The residue (300 mg) was purified asecond time by reverse phase chromatography (YMC-actus Triart Cl 8 1 Ojim30*150mm; mobile phase: gradient from 65% NH4HCO3 0.2% aq, 35% ACN to 25%NH4HCO3 0.2% aq, 75% ACN). The pure fractions were collected, evaporated to drynessyielding 104 mg of compound 224.

References: [1]Patent: WO2018/50686,2018,A1 .Location in patent: Page/Page column 173; 174.

15
[ 1339452-16-2 ]
[ 75-16-1 ]
[ 137890-05-2 ]