[ CAS No. 113808-86-9 ] {[proInfo.proName]}

Name: 113808-86-9|3,5-Dimethylpyrazole-4-carboxylic Acid|97%
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Quality Control of [ 113808-86-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 113808-86-9 ]

CAS No. :	113808-86-9	MDL No. :	MFCD00159642
Formula :	C₆H₈N₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	IOOWDXMXZBYKLR-UHFFFAOYSA-N
M.W :	140.14	Pubchem ID :	2776164
Synonyms :

Calculated chemistry of [ 113808-86-9 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.33
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	35.48
TPSA :	65.98 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.77 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.59
Log Po/w (XLOGP3) :	0.54
Log Po/w (WLOGP) :	0.72
Log Po/w (MLOGP) :	-0.02
Log Po/w (SILICOS-IT) :	1.19
Consensus Log Po/w :	0.6

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-1.35
Solubility :	6.22 mg/ml ; 0.0444 mol/l
Class :	Very soluble
Log S (Ali) :	-1.5
Solubility :	4.46 mg/ml ; 0.0318 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.36
Solubility :	6.17 mg/ml ; 0.0441 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.33

Safety of [ 113808-86-9 ]

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

Application In Synthesis of [ 113808-86-9 ]

* 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 [ 113808-86-9 ]
Downstream synthetic route of [ 113808-86-9 ]

[ 113808-86-9 ] Synthesis Path-Upstream 1~2

1
[ 603-69-0 ]
[ 113808-86-9 ]

Reference： [1] Journal of the American Chemical Society, 2011, vol. 133, # 31, p. 11888 - 11891

2
[ 35691-93-1 ]
[ 113808-86-9 ]

Reference： [1] Zeitschrift fur Physikalische Chemie, 2013, vol. 227, # 6-7, p. 841 - 856

[ 113808-86-9 ] Synthesis Path-Downstream 1~23

1
[ 113808-86-9 ]
[ 75-36-5 ]
1-acetyl-3,5-dimethyl-1<i>H</i>-pyrazole-4-carboxylic acid [ No CAS ]

Reference： [1]Chemische Berichte,1935,vol. 68,p. 1913,1922

2
[ 113808-86-9 ]
[ 67-51-6 ]
[ 15719-64-9 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1894,vol. 279,p. 240

3
3.5-dimethyl-pyrazole-carboxylic acid-⁽⁴⁾-ethyl ester [ No CAS ]
[ 113808-86-9 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1894,vol. 279,p. 240

4
[ 113808-86-9 ]
[ 7732-18-5 ]
[ 67-51-6 ]
[ 15719-64-9 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1894,vol. 279,p. 240

5
[ 863630-51-7 ]
[ 113808-86-9 ]
C₂₀H₂₇N₃O₂ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 5537 - 5542

6
[ 863630-52-8 ]
[ 113808-86-9 ]
C₂₁H₂₉N₃O₂ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 5537 - 5542

7
[ 113808-86-9 ]
C₁₆H₁₅Cl₃N₂*2ClH [ No CAS ]
C₂₂H₂₁Cl₃N₄O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In acetonitrile; at 25.0℃; for 18.0h;	Preparation of Examples 251-253; The piperazine Example 1 (220 mg), EDC (i.e., 1-(3- dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride) (245 mg), HOBT (i.e., 1-hydroxybenzotriazole) (172 mg), acid (108 mg), and JPr2NEt (206 mg) were taken up in CH3CN and stirred at 25C (18 h). The solution was partitioned15 between EtOAc and 1 N NaOH(aq.). The aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine and dried (MgSO4). Filtration and concentration gave a solid. The solid was triturated with Et2O. The white solid was collected and dried to give 125 mg (42 %) of Example 251.

Reference： [1]Patent: WO2006/60461,2006,A1 .Location in patent: Page/Page column 132

8
[ 113808-86-9 ]
[ 172739-04-7 ]
[ 946488-54-6 ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine; In N,N-dimethyl-formamide; at 20.0℃;	EXAMPLE 11; [4-(5-{3-[(1-Acetyl-piperidine-4-carbonyl)-(3-chloro-4-methyl-phenyl)-amino]-propyl}-hexahydro-pyrrolo[3,4-c]pyrrole-2-carbonyl)-3,5-dimethyl-pyrazol-1-yl]-acetic acid trifluoro acetate (II-18); step 1-; A mixture of <strong>[113808-86-9]3,5-dimethyl-1H-pyrazole-4-carboxylic acid</strong> (820 mg; CAS Reg No. 113808-86-9), 11a (2.42 g), TEA (2.2 mL) and PyBOP (5.84 g) in DMF (15 mL) was stirred at RT overnight. The reaction was quenched by addition of water and partitioned between water and EtOAc. The organic layer was separated and washed 3 times with water and once with brine, dried (MgSO4), filtered and evaporated. The residue was purified via SiO2 chromatography eluting with DCM/MeOH/NH4OH to afford 0.829 g of 62a.

Reference： [1]Patent: US2007/191335,2007,A1 .Location in patent: Page/Page column 32-33

9
[ 113808-86-9 ]
[ 1044588-31-9 ]
[ 1044586-80-2 ]

Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 4028 - 4037

10
[ 603-69-0 ]
[ 113808-86-9 ]

Reference： [1]Journal of the American Chemical Society,2011,vol. 133,p. 11888 - 11891

11
[ 10196-18-6 ]
[ 113808-86-9 ]
3,5-dimethyl-4-carboxypyrazole [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2011,vol. 133,p. 11888 - 11891

12
[ 113808-86-9 ]
copper(II) choride dihydrate [ No CAS ]
[ 68-12-2 ]
[Cu₂(dmcapz)₂OH₂]_n.1.5n(DMF)0.1n(H₂dmcapz) [ No CAS ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 13117 - 13125

13
[ 35691-93-1 ]
[ 113808-86-9 ]

Reference： [1]Zeitschrift fur Physikalische Chemie,2013,vol. 227,p. 841 - 856

14
[ 113808-86-9 ]
[ 14404-41-2 ]
[ 68-12-2 ]
[Cr₃O(3,5-dimethyl-1H-pyrazole-4-carboxylic acid(-1H))₆(N,N-dimethylformamide)₃]⊃N,N-dimethylformamide [ No CAS ]

Reference： [1]Inorganic Chemistry,2014,vol. 53,p. A9870 - A9875

15
[ 113808-86-9 ]
5-piperazin-1-ylmethyl-thiophene-2-carboxylic acid (2-methoxy-pyridin-ylmethyl)amide hydrochloride [ No CAS ]
[ 76-05-1 ]
5-[4-(3,5-dimethyl-1H-pyrazole-4-carbonyl)-piperazin-1-ylmethyl]-thiophene-2-carboxylic acid (2-methoxy-pyridin-4-ylmethyl)-amide trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%		Example 139: 5-[4-(3,5-Dimethyl-1 H-pyrazole-4-carbonyl)-piperazin-1 -ylmethyl]- thiophene-2-carboxylic acid (2-methoxy-pyridin-4-ylmethyl)-amide trifluoroacetate To a solution of 3,5-dimethyl-1 H-pyrazole-4-carboxylic acid (18 mg, 0.13 mmol), HOBt*H2O (0.13 mmol), N-Methylmorpholine (1 mmol), 4-Dimethylaminopyridine (0.01 mmol) in 0.75 ml_ of DMF, a solution of intermediate 5 (0.1 1 mmol in 1 ml_ DMF) was added followed by EDC (neat, 0.13 mmol). The tube was closed with a screw cap and shaken over night at 40 C. 0.1 ml TFA was added and the volume was adjusted to 2.2 ml with DMF. The solution was filtered and submitted to preparative RP-HPLC purification to give 5-[4-(3,5-Dimethyl-1 H-pyrazole-4-carbonyl)-piperazin-1 -ylmethyl]- thiophene-2-carboxylic acid (2-methoxy-pyridin-4-ylmethyl)-amide trifluoroacetate as a colorless film (33 mg, 52%). 1 H NMR (DMSO-d6, 500 MHz) d ppm 9.22 (t, 1 H), 8.1 (d, 1 H), 7.80 (d, 1 H), 7.30 (bs, 1 H), 6.90 (d, 1 H), 6.69 (s, 1 H), 4.6 (bs, 2H), 4.40 (bs, 2H), 4.3-3.7 (broad signal, 4H), 3.7 (s, 3H), 3.5-3.0 (broad signal, 4H), 2.13 (s, 6H). LC/MS (Method 3); Rt = 1 .15 min; detected mass: m/z = 469.31 ([M+H]+)

Reference： [1]Patent: WO2015/82474,2015,A1 .Location in patent: Page/Page column 52; 53

16
[ 113808-86-9 ]
5-piperazin-1-ylmethyl-thiophene-2-carboxylic acid (2-methoxypyridin-4-ylmethyl)amide hydrochloride [ No CAS ]
[ 76-05-1 ]
5-[4-(3,5-dimethyl-1H-pyrazole-4-carbonyl)piperazin-1-ylmethyl]thiophene-2-carboxylic acid (2-methoxypyridin-4-ylmethyl)amide trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%		To a solution of <strong>[113808-86-9]3,5-dimethyl-1H-pyrazole-4-carboxylic acid</strong> (18 mg, 0.13 mmol), HOBt*H2O (0.13 mmol), N-Methylmorpholine (1 mmol), 4-Dimethylaminopyridine (0.01 mmol) in 0.75 mL of DMF, a solution of intermediate 5 (0.11 mmol in 1 mL DMF) was added followed by EDC (neat, 0.13 mmol). The tube was closed with a screw cap and shaken over night at 40 C. 0.1 ml TFA was added and the volume was adjusted to 2.2 ml with DMF. The solution was filtered and submitted to preparative RP-HPLC purification to give 5-[4-(3,5-Dimethyl-1 H-pyrazole-4-carbonyl)-piperazin-1-ylmethyl]-thiophene-2-carboxylic acid (2-methoxy-pyridin-4-ylmethyl)-amide trifluoroacetate as a colorless film (33 mg, 52%). 1 H NMR (DMSO-d6, 500 MHz) d ppm 9.22 (t, 1 H), 8.1 (d, 1 H), 7.80 (d, 1 H), 7.30 (bs, 1 H), 6.90 (d, 1 H), 6.69 (s, 1 H), 4.6 (bs, 2H), 4.40 (bs, 2H), 4.3-3.7 (broad signal, 4H), 3.7 (s, 3H), 3.5-3.0 (broad signal, 4H), 2.13 (s, 6H). LC/MS (Method 3); Rt = 1.15 min; detected mass: m/z = 469.31 ([M+H]+)

Reference： [1]Patent: EP2881390,2015,A1 .Location in patent: Paragraph 0090

17
[ 51784-73-7 ]
[ 113808-86-9 ]
(4-benzothiazol-2-yl-piperidin-1-yl)-(3,5-dimethyl-1h-pyrazol-4-yl)-methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20.0℃;	A mixture of <strong>[113808-86-9]3,5-dimethyl-1H-pyrazole-4-carboxylic acid</strong> (9.6 mg, 0.069 mmol, Maybridge), piperidin-4-yl-benzothiazole (15 mg, 0.069 mmol, Compound 2h, Step 2), Hunig?s base (24 tL, 0.137 mmol) and HATU (39 mg, 0.103 mmol) was stirred overnight at room temperature in DMF (343 .iL). The reaction was purified directly by prep HPLC to give a pale yellow solid after freeze drying from dioxane (11.5 mg, 50 % yield). LCMS (ESI) m/z 341.4 (M+1) retention time 3.8 mm. ?HNMR (300MHz, CD3OD) oe = 7.95 (m, 2H), 7.50 (m, 1H), 7.44-7.38 (m, 1H), 3.55-3.41 (m, 1H), 3.3 1-3.01 (m, 2H), 2.50 (m, 2H),2.30 (s, 6H), 2.26-2. 12 (m, 2H), 1.95-1.78 (m, 2H).

Reference： [1]Patent: WO2015/153554,2015,A1 .Location in patent: Page/Page column 62

18
[ 113808-86-9 ]
2-(((3R,4S)-3-fluoropiperidin-4-yl)oxy)-5-(4-((4-(4-(oxetan-3-yl)piperazin-1-yl)phenyl)amino)-1,3,5-triazin-2-yl)benzonitrile [ No CAS ]
2-(((3R,4S)-1-(3,5-dimethyl-1H-pyrazole-4-carbonyl)-3-fluoropiperidin-4-yl)oxy)-5-(4-((4-(4-(oxetan-3-yl)piperazin-1-yl)phenyl)amino)-1,3,5-triazin-2-yl)benzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20.0℃; for 2.0h;	Example 135 2-(((3R,4S)-1-(3,5-dimethyl-1H-pyrazole-4-carbonyl)-3-fluoropiperidin-4-yl)oxy)-5-(4-((4-(4-(oxetan-3-yl)piperazin-1-yl)phenyl)amino)-1,3,5-triazin-2-yl)benzonitrile To a solution of 2-(((3R,4S)-3-fluoropiperidin-4-yl)oxy)-5-(4-((4-(4-(oxetan-3-yl)piperazin-1-yl)phenyl)amino)-1,3,5-triazin-2-yl)benzonitrile (35 mgs, 0.07 mmol) in DMF (1.0 mL) was added 3,5-Dimethyl-1H-pyrazole-4-carboxylic acid (19 mgs, 0.13 mmol), HATU (50 mgs, 0.13 mmol) and TEA (0.02 mL, 0.13 mmol). The above reaction mixture was stirred at room temperature for 2 h, evaporated under reduced pressure and purified via preparative HPLC (5-65% acetonitrile in water, 0.1% trifluoroacteic acid buffer) to yield the title compound. LCMS-ESI+ (m/z): [M+H]+ calcd for C34H37FN10O3: 652.7. found: 653.3 1H NMR (400 MHz, DMSO-d6) delta 10.74 (brs, 1H), 10.24-10.09 (m, 1H), 8.75 (s, 1H), 8.57 (m, 2H), 7.67-7.43 (m, 3H), 7.06 (d, J=9.6 Hz, 2H), 5.26-5.01 (m, 3H), 4.76 (m, 4H), 4.44 (m, 1H), 4.27-3.61 (m, 5H), 3.59-3.40 (m, 2H), 3.10-2.88 (m, 4H), 2.50 (s, 6H), 2.02-1.97 (m, 2H).

Reference： [1]Patent: US2016/96827,2016,A1 .Location in patent: Paragraph 0629; 0630; 0631

19
[ 113808-86-9 ]
[ 142-71-2 ]
[Cu(3,5-dimethylpyrazol-4-carboxylate)₂] [ No CAS ]