29097-00-5|Methyl 3-amino-1H-pyrazole-4-carboxylate| Ambeed

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Quality Control of [ 29097-00-5 ] Purity: 95% SDS Specification

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Product Details of [ 29097-00-5 ]

CAS No. :	29097-00-5
Formula :	C₅H₇N₃O₂
M.W :	141.13
SMILES Code :	O=C(C1=CNN=C1N)OC
MDL No. :	MFCD02936636
InChI Key :	KGQFAPZUQKYADG-UHFFFAOYSA-N
Pubchem ID :	272904

Safety of [ 29097-00-5 ]

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

Computational Chemistry of [ 29097-00-5 ] Show Less

Physicochemical Properties

Num. heavy atoms	10
Num. arom. heavy atoms	5
Fraction Csp3	0.2
Num. rotatable bonds	2
Num. H-bond acceptors	3.0
Num. H-bond donors	2.0
Molar Refractivity	34.27
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	81.0 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.74
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	0.27
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	-0.21
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.	-0.55
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	0.11
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.07

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.12
Solubility	10.6 mg/ml ; 0.0753 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.	-1.53
Solubility	4.14 mg/ml ; 0.0294 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	-0.93
Solubility	16.7 mg/ml ; 0.119 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	No
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.	-6.97 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)	1.52

Application In Synthesis of [ 29097-00-5 ]

* 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 [ 29097-00-5 ]

[ 29097-00-5 ] Synthesis Path-Downstream 1~31

1
[ 74-89-5 ]
[ 29097-00-5 ]
[ 77937-05-4 ]

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 3019 - 3029.

2
[ 67-56-1 ]
[ 41680-34-6 ]
[ 29097-00-5 ]

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 3019 - 3029.

4
ethyl ω, ω, ω-trifluoroacetoacetate [ No CAS ]
[ 29097-00-5 ]
methyl 5-hydroxy-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With PPA; In water;	a) A mixture of 11.5 g of <strong>[29097-00-5]methyl 5-aminopyrazole-4-carboxylate</strong>, 16 ml of ethyl omega, omega, omega-trifluoroacetoacetate and 150 g of polyphosphoric acid was heated to 100 while stirring for 16 hours. After cooling to 20, cold water was added and the mixture was extracted with ethyl acetate. The organic phase was washed with 1N aqueous hydrochloric acid and aqueous saturated sodium chloride solution and then dried over Na2 SO4. The solvent was evaporated in a vacuum and the residue was taken up in ether. The solid product was filtered off under suction and recrystallized from 2-propanol. There was obtained an isomer of the product, namely methyl 7-hydroxy-5-(trifluoromethyl)pyrazolo-[1,5-a]pyrimidine-3-carboxylate of m.p. 216-217. The product enriched in the mother liquors was crystallized from ethyl acetate. There was obtained methyl 5-hydroxy-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-3-carboxylate of m.p. 149-150.

References: [1]Patent: US5036064,1991,A .

5
[ 29097-00-5 ]
[ 115955-48-1 ]
C₁₄H₁₀N₄O₄ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 2735 - 2738.

6
[ 92-79-5 ]
[ 29097-00-5 ]
[ 1204702-15-7 ]

Yield	Reaction Conditions	Operation in experiment
80%		1.0 g of compound (2') is added to 10 ml of phosphoric acid to dissolve. This solution is ice-cooled to keep the temperature to -5 to 0C, and 0.54 g of sodium nitrite is added thereto, followed by stirring for 1 hour to obtain a diazonium salt solution. Separately, 20 ml of NMP (N- methylpyrrolidone) is added to 1.60 g of compound (3') and, under stirring, the aforesaid diazonium salt solution is added thereto at 8C or lower. Simultaneously with completion of the addition, the ice bath is removed, and stirring is continued for further 1 hour. 40 ml of methanol is added to the reaction solution, and the resulting mixture is stirred for 30 minutes. Crystals precipitated are collected by filtration, and spray-washed with 30 ml of methanol. The thus- obtained crystals are added, without drying, to 100 ml of water, followed by stirring at 20 to 25C for 30 minutes. Crystals precipitated are collected by filtration, and sufficiently spray-washed with water. The thus-obtained crystals are added, without drying, to 20 ml of NMP and 10 ml of water, followed by stirring for 30 minutes under heating at 100C. After stirring for 30 minutes at room temperature, crystals precipitated are collected by filtration, and spray-washed with 20 ml of NMP/water=2/l and 20 ml of water. The thus-obtained crystals are dried to obtain 2.0 g of compound D-228 of the invention. Yield: 80%.Infrared absorption chart is shown in Fig. 6.

References: [1]Patent: WO2011/87148,2011,A1 .Location in patent: Page/Page column 91-92.

7
[ 92-15-9 ]
[ 104-88-1 ]
[ 29097-00-5 ]
methyl-5-(4-chlorophenyl)-7-hydroxy-6-[(2-methoxyphenyl)amino]carbonyl}-7-methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%	In ethanol; at 25℃; for 1.5h;Sonication;	General procedure: A mixture of aminoazole 1c-e (1 mmol), acetoacetamide 2a,b,d (1 mmol), and aromatic aldehyde 3b,d-g (1 mmol) in 10 mL of ethanol was ultrasonicated at room temperature for 90 min in a round-bottom flask equipped with a condenser. The reaction mixture was allowed to stand up to 12 h at room temperature and then was filtered out to give the solid compounds 6a-e, which were washed with ethanol and air dried. Reaction products were obtained in high purity and did not require further purification by recrystallization.

References: [1]Tetrahedron,2011,vol. 67,p. 9389 - 9400.

8
[ 92-15-9 ]
[ 104-88-1 ]
[ 29097-00-5 ]
[ 1349163-36-5 ]

Yield	Reaction Conditions	Operation in experiment
50%	In N,N-dimethyl-formamide; for 0.166667h;Reflux;	General procedure: A mixture of aminoazole 1c-e (1 mmol), acetoacetamide 2a,b,d (1 mmol), and aromatic aldehyde 3b,d-g (1 mmol) in 0.1 mL of DMF was heated to reflux for 10 min. After cooling acetone (10 mL) was added. The precipitate formed was filtered out to give the solid dihydropyrimidines 7a-e, which were washed with acetone and air dried.

References: [1]Tetrahedron,2011,vol. 67,p. 9389 - 9400.

9
[ 29096-99-9 ]
[ 29097-00-5 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrazine hydrate; In ethanol; at 20 - 75℃;	100 g (645 mmol) of methyl (2E/Z)-2-cyano-3-ethoxyacrylate were initially charged in 481 ml of ethanol. 31 ml (645 mmol) of an 85% strength hydrazine hydrate solution were then added dropwise at room temperature with cooling (exothermal temperature.) over a period of 45 minutes. The mixture was stirred at 75 C. for another 12 hours. The hot mixture was filtered and the organic phase was concentrated under reduced pressure. This gave 64 g of methyl 5-amino-1H-pyrazole-4-carboxylate (log P =-0.07; HPLC content: 86%).

References: [1]Patent: US2008/287463,2008,A1 .Location in patent: Page/Page column 46.

10
[ 65210-56-2 ]
[ 29097-00-5 ]
methyl 7-oxopyrazolo[1,5-a]pyrimidine-3-carboxylate [ No CAS ]
C₉H₁₁N₃O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.4 g	With acetic acid; for 24h;Reflux;	Diethylamine (2.8 mL, 27 mmol) was added to a cold solution of 1 (1.8 mL, 20 mmol) in dichloromethane (60 mL) at 0 C and the so formed solution was stirred at 0 C for 5 h and the volatile components were evaporated in vacuo (30 C, 20 mbar). The crude enamino ester 2, which was obtained as yellow oil, was dissolved in acetic acid (45 mL), aminopyrazole 3 (2.8 g, 20 mmol) was added and the mixture was heated under reflux for 24 h. Volatile components were evaporated in vacuo (40 C, 7 mbar) and the residue was triturated with warm water (60 C, 50 mL). The precipitate was collected by filtration and washed with ethanol (15 mL) to give a 1:3 mixture of 4 and 5 (?2 g). Subsequent crystallization from ethanol afforded the title compound 5 0.40 g (10%) as a pale yellow solid; mp 280-287 C; [Found: C, 49.67; H, 3.40; N, 21.64. C8H7N3O3 requires: C, 49.74; H, 3.65; N, 21.75%]; numax (ATR) 3068, 2963, 1699, 1624, 1575, 1504, 1468, 1433, 1411, 1391, 1249, 1209, 1150, 1123, 1069, 1017, 944, 904, 876, 800, 772, 719, 631 cm-1; deltaH (500 MHz, DMSO-d6) 3.83 (3H, s, OMe), 5.95 (1H, d, J=7.5 Hz, 6-H), 7.85 (1H, d, J=7.5 Hz, 5-H), 8.25 (1H, s, 2-H), 12.24 (1H, br s, 4-H); deltaC (126 MHz, DMSO-d6) 51.5, 96.7, 99.1, 140.6, 142.9, 143.5, 155.8; HRMS (ESI): MH+, found 194.0557. C8H8N3O3 requires 194.0566.

References: [1]Tetrahedron,2014,vol. 70,p. 8267 - 8279.

11
[ 18856-69-4 ]
[ 29097-00-5 ]
dimethyl 7-oxo-4,7-dihydropyrazolo[1,5-a]pyrimidine-3,6-dicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1.04 g	With acetic acid; for 5h;Reflux;	General procedure: A mixture of dialkyl malonate (10 mmol), anhyd toluene (25 mL), and N,N-dimethylformamide dimethylacetal (DMFDMA) (1.6 mL, 12 mmol) was heated under reflux for 2 h, cooled, and volatile components were evaporated in vacuo. The crude enamino ester 6 was dissolved in acetic acid (30 mL), aminopyrazole 3 (1.4 g, 10 mmol) was added and the mixture was heated under reflux for 5 h. The reaction mixture was cooled to rt and the precipitate was collected by filtration and washed with ethanol (2×10 mL) to give the title compound 7. The following compounds were prepared in this manner.

References: [1]Tetrahedron,2014,vol. 70,p. 8267 - 8279.

12
[ 950171-60-5 ]
[ 29097-00-5 ]
6-benzyl 3-methyl 7-oxo-4,7-dihydropyrazolo[1,5-a]pyrimidine-3,6-dicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1.3 g	With acetic acid; for 5h;Reflux;	General procedure: A mixture of dialkyl malonate (10 mmol), anhyd toluene (25 mL), and N,N-dimethylformamide dimethylacetal (DMFDMA) (1.6 mL, 12 mmol) was heated under reflux for 2 h, cooled, and volatile components were evaporated in vacuo. The crude enamino ester 6 was dissolved in acetic acid (30 mL), aminopyrazole 3 (1.4 g, 10 mmol) was added and the mixture was heated under reflux for 5 h. The reaction mixture was cooled to rt and the precipitate was collected by filtration and washed with ethanol (2×10 mL) to give the title compound 7. The following compounds were prepared in this manner.

References: [1]Tetrahedron,2014,vol. 70,p. 8267 - 8279.

13
[ 4637-24-5 ]
[ 105-34-0 ]
[ 29097-00-5 ]