5932-32-1|1,4,5,6-Tetrahydrocyclopenta[c]pyrazole-3-carboxylic acid| Ambeed

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Quality Control of [ 5932-32-1 ] Purity: 98% SDS Specification

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Product Details of [ 5932-32-1 ]

CAS No. :	5932-32-1
Formula :	C₇H₈N₂O₂
M.W :	152.15
SMILES Code :	O=C(C1=NNC2=C1CCC2)O
MDL No. :	MFCD01248822
InChI Key :	FCYBBDFUBSEGMX-UHFFFAOYSA-N
Pubchem ID :	776416

Safety of [ 5932-32-1 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338

Computational Chemistry of [ 5932-32-1 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	5
Fraction Csp3	0.43
Num. rotatable bonds	1
Num. H-bond acceptors	3.0
Num. H-bond donors	2.0
Molar Refractivity	38.17
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	65.98 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.45
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	0.76
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.6
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.	0.33
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	1.49
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.73

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.53
Solubility	4.46 mg/ml ; 0.0293 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.	-1.73
Solubility	2.86 mg/ml ; 0.0188 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	-1.42
Solubility	5.76 mg/ml ; 0.0378 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.	-6.69 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.	0.56

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)	2.28

Application In Synthesis of [ 5932-32-1 ]

* 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.

Downstream synthetic route of [ 5932-32-1 ]

[ 5932-32-1 ] Synthesis Path-Downstream 1~35

1
[ 5932-32-1 ]
[ 2214-03-1 ]

References: [1]Justus Liebigs Annalen der Chemie,1938,vol. 536,p. 97,108.

2
[ 5932-31-0 ]
[ 5932-32-1 ]

References: [1]Organic Process Research and Development,2009,vol. 13,p. 543 - 547.
[2]Journal of Medicinal Chemistry,2008,vol. 51,p. 5101 - 5108.
[3]Journal of Medicinal Chemistry,2003,vol. 46,p. 3945 - 3951.
[4]Justus Liebigs Annalen der Chemie,1938,vol. 536,p. 97,108.
[5]Justus Liebigs Annalen der Chemie,1938,vol. 536,p. 97,108.

4
[ 120-92-3 ]
(CH₃)2N-(CH=CH)2-CH(Y)N(CH₃)2, Y=N(CH₃)2 and OCH₃ [ No CAS ]
[ 5932-32-1 ]

References: [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 3945 - 3951.

5
(2-oxocyclopentyl)glycoxylic acid ethyl ester sodium salt [ No CAS ]
[ 5932-32-1 ]

References: [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 3945 - 3951.

6
[ 39163-39-8 ]
[ 5932-32-1 ]

References: [1]Justus Liebigs Annalen der Chemie,1938,vol. 536,p. 97,108.

7
[ 120-92-3 ]
[ 5932-32-1 ]

References: [1]Justus Liebigs Annalen der Chemie,1938,vol. 536,p. 97,108.

8
[ 5932-32-1 ]
[ 84597-86-4 ]

References: [1]Justus Liebigs Annalen der Chemie,1938,vol. 536,p. 97,108.

9
[ 5932-32-1 ]
[ 84597-85-3 ]

References: [1]Justus Liebigs Annalen der Chemie,1938,vol. 536,p. 97,108.

10
[ 100568-79-4 ]
[ 5932-32-1 ]
7,7-dimethyl-2-(1,4,5,6-tetrahydro-cyclopentapyrazol-3-yl)-5,7-dihydro-3H-imidazo[4,5-f]indol-6-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
16%		EXAMPLE 1 7,7-Dimethyl-2-(1,4,5,6-tetrahydro-cyclopentapyrazol-3-yl)-5,7-dihydro-3H-imidazo[4,5-f]indol-6-one 5,6-Diamino-3,3-dimethyl-1,3-dihydro-indol-2-one (143 mg, 0.75 mmol), and 1,4,5,6-Tetrahydro-cyclopentapyrazole-3-carboxylic acid (114 mg, 0.75 mmol) were mixed with polyphosphoric acid (5.10 g, 53.12 mmol) and phosphorus pentoxide (190 mg, 1.34 mmol) and stirred under nitrogen at 150 C. for 6 h. The mixture was quenched with ice water (25 ml) and the resulting solution was adjusted to pH 7-8 by adding aqueous ammonia and then extracted twice with ethyl acetate (3*50 ml). The combined organic layers were washed with water (50 ml), dried over sodium sulfate and concentrated. The crude product was purified by HPL chromatography. Yield 37 mg (16%) of a light brown solid. MS: M=308.1 (API+) 1H-NMR (400 MHz, D6-DMSO): δ (ppm)=1.29 (s, 6H), 2.52 (m, 2H), 2.71 (m, 2H), 2.81 (m, 2H), 6.88 (br, 1H), 6.95 (br, 1H), 10.23 (br, 1H)

References: [1]Patent: US2006/235013,2006,A1 .Location in patent: Page/Page column 18.

11
[ 5932-32-1 ]
[ 851776-30-2 ]

References: [1]Organic Process Research and Development,2009,vol. 13,p. 543 - 547.

12
[ 1044588-31-9 ]
[ 5932-32-1 ]
[ 1044586-75-5 ]

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

13
[ 5932-32-1 ]
C₂₀H₁₈Cl₂N₄O [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 393 - 397.

14
[ 5932-32-1 ]
C₁₉H₁₄Cl₂F₂N₄O [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 393 - 397.

15
[ 5932-32-1 ]
C₁₉H₁₅Cl₂FN₄O [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 393 - 397.

16
[ 5932-32-1 ]
C₁₄H₁₁Cl₃N₂O [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 393 - 397.

17
[ 94-99-5 ]
[ 5932-32-1 ]
C₁₄H₁₂Cl₂N₂O₂ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 393 - 397.

18
[ 67-56-1 ]
[ 5932-32-1 ]
methyl cyclopenta[c]pyrazole-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With sulfuric acid; at 85℃; for 18h;	To a solution of cyclopenta[c]pyrazole-3-carboxylic acid (8.00 g, 52.6 mmol) in MeOH (80 mL) was added H2SO4 (5.16 g, 52.6 mmol, 2.80 mL) at 25 C. The mixture was heated to 85 C and stirred for 18 hrs. TLC indicated that the reaction was complete. The reaction was quenched by NaHCO3 (60 mL) at 0 C and concentrated under reduced pressure to remove MeOH. The aqueous phase was extracted with EtOAc (50 mL x 3). The combined organic phase was washed with saturated brine (50 mL x 2), dried with anhydrous Na2SO4, filtered and concentrated under reduced pressure to give methyl cyclopenta[c]pyrazole-3-carboxylate (6.00 g, 36.1 mmol, 69% yield) as a white solid. 1H NMR: CDCl3 400MHz CDCl3 = 3.86 (d, J=14.8 Hz, 3H), 2.86 -2.71 (m, 4H), 2.50 -2.43 (m, 2H). ESI-MS (m/z): 167.0 (M+H)+

References: [1]Patent: WO2017/120429,2017,A1 .Location in patent: Page/Page column 266.

19
[ 5932-32-1 ]
(x)C₂HF₃O₂*C₂₇H₃₅FN₄O₄ [ No CAS ]

References: [1]Patent: WO2020/41100,2020,A1 .

20
[ 5932-32-1 ]
2-(3-((2R,6S)-2,6-dimethylmorpholine-4-carbonyl)-5,6-dihydrocyclopenta[c]pyrazol-1(4H)-yl)acetic acid [ No CAS ]

References: [1]Patent: WO2020/41100,2020,A1 .
[2]Patent: WO2020/92183,2020,A1 .

21
[ 5932-32-1 ]
1-(4-(cyclopentyloxy)piperidin-1-yl)-2-(3-((2S,6R)-2,6-dimethylmorpholine-4-carbonyl)-5 6-dihydrocyclopenta[c]pyrazol-1(4H)-yl)ethan-1-one [ No CAS ]

References: [1]Patent: WO2020/41100,2020,A1 .

22
[ 5932-32-1 ]
1-(4-benzyl-4-fluoropiperidin-1-yl)-2-(3-((2S,6R)-2,6-dimethylmorpholine-4-carbonyl)-5 6-dihydrocyclopenta[c]pyrazol-1(4H)-yl)ethan-1-one [ No CAS ]

References: [1]Patent: WO2020/41100,2020,A1 .

23
[ 5932-32-1 ]
tert-butyl 2-(3-((2R,6S)-2,6-dimethylmorpholine-4-carbonyl)-5,6- dihydrocyclopenta[c]pyrazol-1(4H)-yl)acetate [ No CAS ]

References: [1]Patent: WO2020/41100,2020,A1 .
[2]Patent: WO2020/92183,2020,A1 .

24
[ 5932-32-1 ]
2-(3-(cis-2,6-dimethylmorpholine-4-carbonyl)-5,6-dihydrocyclopenta[c]pyrazol-1(4H)-yl)-1-(4-hydroxypiperidin-1-yl)ethanone [ No CAS ]

References: [1]Patent: WO2020/41100,2020,A1 .

25
[ 5932-32-1 ]
cis-2,6-dimethylmorpholine [ No CAS ]
((2R,6S)-2,6-dimethylmorpholino)(1,4,5,6-tetrahydrocyclopenta[c]pyrazol-3- yl)methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 0 - 20℃; for 2.5h;	To a solution of <strong>[5932-32-1]1,4,5,6-tetrahydrocyclopenta[c]pyrazole-3-carboxylic acid</strong> (1.65 g, 10.84 mmol),3H-[1,2,3]triazolo[4,5-b]pyridin-3-ol (1.919 g, 14.10 mmol), and N1- ((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (2.70 g, 14.10 mmol) in DMF (21.69 ml) at 0 oC was added 4-methylmorpholine (2.385 ml, 21.69 mmol) and (2R,6S)-2,6-dimethylmorpholine (1.374 g, 11.93 mmol). Upon completion of the addition, ice- water bath was removed and the mixture was stirred at RT for 2.5 h. To this mixture was added 150 mL water, and the mixture was extracted with EtOAc (2x200mL). The organics were washed with brine and dried (Na2SO4), and filtered and concentrated to afford the title compound. LCMS m/z [M+H]+ 249.0.
	With triethylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 3h;	To a mixture of <strong>[5932-32-1]1,4,5,6-tetrahydrocyclopenta[c]pyrazole-3-carboxylic acid</strong> (A-3) (2.50 g, 16.43 mmol) in DMF (16.43 ml) at ambient temperature were added TEA (2.75 ml, 19.72 mmol), HATU (7.50 g, 19.72 mmol), and (2R,6S)-2,6-dimethylmorpholine (2.84 g, 24.65 mmol). The mixture stirred for 3 h before acidifying with AcOH (5 mL). The mixture was purified directly by column chromatography on C18 column (5-95% ACN/water with 0.05% TFA modifier) to afford the title compound. MS: 250.3 (M+1).
		To the stirred suspension of 1,4,5,6-tetrahydrocyclopenta[c]pyrazole-3- carboxylic acid (2000 mg, 13.14 mmol) in DCM (25 mL) and DMF (25.00 mL) were added HOAt (2684 mg, 19.72 mmol) and EDC (3780 mg, 19.72 mmol). The mixture was stirred at RT for about 20 min until most solids going into solution, then (2S,6R)-2,6-dimethylmorpholine (3028 mg, 26.3 mmol) was added. The mixture was stirred at RT for about 2 h. The mixture turned clear. LC-Mass showed the desired product as the major product. The mixture was concentrated and loaded onto RediSep C18415 g gold column and purified by Teledyne Isco system using 0%-100% ACN (buffering with 0.05% TFA) /water (0.05% TFA) as eluent. The title compound was collected as a solid after lyophilization. LCMS m/z (M+H) calc’d: 250.15; found (M+H) : 250.21

With 4-methyl-morpholine; 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 0 - 20℃;

To a mixture of <strong>[5932-32-1]1,4,5,6-tetrahydrocyclopenta[c]pyrazole-3-carboxylic acid</strong> (25.74 g, 169 mmol), EDC (42.2 g, 220 mmol) and 1-hydroxy-7-azabenzotriazole (23.03 g, 169 mmol) in DMF (85 ml) at 0 C was added 4-methylmorpholine (37.2 ml, 338 mmol) and cis-2,6- dimethylmorpholine (21.43 g, 186 mmol). Upon completion of the addition, ice-water was removed. The mixture was stirred at RT overnight. To this mixture was added 300 ml of water slowly and the resulting suspension was stirred at RT for 30 min. A solid was obtained by filtration, followed by washing with water (3x 10 mL), drying under reduced pressure and N2 to afford the title compound, which was used without further purification. MS: 250.3 [M+H]+.

References: [1]Patent: WO2020/41100,2020,A1 .Location in patent: Page/Page column 46.
[2]Patent: WO2020/81381,2020,A1 .Location in patent: Page/Page column 36-37.
[3]Patent: WO2020/92183,2020,A1 .Location in patent: Page/Page column 38; 40.
[4]Patent: WO2020/112581,2020,A1 .Location in patent: Page/Page column 74; 75.

26
[ 396091-35-3 ]
[ 5932-32-1 ]
(4-((tert-butyldiphenylsilyl)oxy)piperidin-1-yl)(1,4,5,6-tetrahydrocyclopenta[c]pyrazol-3-yl)methanone [ No CAS ]