[ CAS No. 159974-63-7 ] {[proInfo.proName]}

Name: 159974-63-7|Methyl 2-(piperazin-1-yl)benzoate|95%
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Quality Control of [ 159974-63-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 159974-63-7 ]

Product Details of [ 159974-63-7 ]

CAS No. :	159974-63-7	MDL No. :	MFCD06656931
Formula :	C₁₂H₁₆N₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XGNPSKXFPSPTDE-UHFFFAOYSA-N
M.W :	220.27	Pubchem ID :	10932975
Synonyms :

Calculated chemistry of [ 159974-63-7 ]

Physicochemical Properties

Num. heavy atoms :	16
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.42
Num. rotatable bonds :	3
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	69.08
TPSA :	41.57 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) :	-6.76 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.11
Log Po/w (XLOGP3) :	1.24
Log Po/w (WLOGP) :	0.12
Log Po/w (MLOGP) :	1.27
Log Po/w (SILICOS-IT) :	1.48
Consensus Log Po/w :	1.25

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.07
Solubility :	1.89 mg/ml ; 0.00858 mol/l
Class :	Soluble
Log S (Ali) :	-1.71
Solubility :	4.29 mg/ml ; 0.0195 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.98
Solubility :	0.232 mg/ml ; 0.00105 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.79

Safety of [ 159974-63-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302+H312+H332-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 159974-63-7 ]

* 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 [ 159974-63-7 ]
Downstream synthetic route of [ 159974-63-7 ]

[ 159974-63-7 ] Synthesis Path-Upstream 1~4

1
[ 67-56-1 ]
[ 446831-27-2 ]
[ 159974-63-7 ]

Yield	Reaction Conditions	Operation in experiment
63%	Stage #1: for 18 h; Reflux	Example 2: Synthesis of 2-{4-[2-(3,5-Dimethyl-pyrazol-l-yl)-acetyl]-piperazin-l-yl}- N-pyridin-4-yl-benzamidee 1 h 16h 2-Piperazin-l-yl-benzoic acid (1.000 g, 4.89 mmol) is suspended in 10 niL of MeOH. To this is added 5 niL of cone. H₂SO₄. The mixture is stirred for 16 h resulting in a white precipitate. An additional 5 rnL of H₂SO₄ is added with an additional 10 rnL of MeOH. The reaction volume is increased by an additional 200 mL of MeOH and 60 mL of H₂SO₄ and the mixture is stirred an additional 2 h and then heated at reflux for 12 h. The reaction volume is then reduced to approximately 175 mL and applied to an ion exchange column, eluting with 5x200 mL of 10percent NH₃/Me0H and then the product fractions are concentrated. The eluent is co-evaporated with toluene to remove residual water to give 0.667 g of 2-piperazin-l-yl -benzoic acid methyl ester in 63percent yield.

Reference： [1] Patent: WO2010/126851, 2010, A1, . Location in patent: Page/Page column 86
[2] Patent: WO2010/126811, 2010, A1, . Location in patent: Page/Page column 142-143

2
[ 110-85-0 ]
[ 610-94-6 ]
[ 159974-63-7 ]

Yield	Reaction Conditions	Operation in experiment
26%	With potassium carbonate In 1,2-dioxacyclohexane; sodium hydroxide	a. 1-(2-carbomethoxyphenyl)-piperazine To a solution of methyl 2-bromobenzoate (1.63 g, 17.8 mmol) in 1,6-dioxane (100 ml) at room temperature was added piperazine (15.3 g, 178 mmol) and K₂CO₃ (4.92 g, 35 mmol). The resulting mixture was heated to reflux for 7 days after which the reaction mixture was cooled to room temperature. The solvent and the excess piperazine were removed in vacuo along with heating with a hot water bath. The residue was dissolved in 1N NaOH solution, extracted with CH₂Cl₂ (6*30 ml), and dried over Na₂SO₄. The solvent was removed in vacuo to obtain 1-(2-carbomethoxyphenyl)-piperazine as a yellow oil (1.0 g, 26percent).

Reference： [1] Patent: US6218390, 2001, B1,

3
[ 110-85-0 ]
[ 610-94-6 ]
[ 584-08-7 ]
[ 159974-63-7 ]

Reference： [1] Patent: US6159990, 2000, A,

4
[ 159974-40-0 ]
[ 159974-63-7 ]

Reference： [1] Tetrahedron Letters, 1994, vol. 35, # 40, p. 7331 - 7334

[ 159974-63-7 ] Synthesis Path-Downstream 1~23

1
[ 159974-40-0 ]
[ 159974-63-7 ]

Reference： [1]Tetrahedron Letters,1994,vol. 35,p. 7331 - 7334

2
[ 159974-63-7 ]
[ 200052-52-4 ]
6-(3,4-Difluoro-phenyl)-1-{5-[4-(2-methoxycarbonyl-phenyl)-piperazin-1-yl]-pentyl}-2,4-dimethyl-1,6-dihydro-pyrimidine-5-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 4804 - 4813

3
[ 159974-63-7 ]
[ 200051-89-4 ]
4-(3,4-difluoro-phenyl)-3-{3-[4-(2-methoxycarbonyl-phenyl)-piperazin-1-yl]-propylcarbamoyl}-6-methyl-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 4794 - 4803

4
[5-(4-chloro-phenyl)-2<i>H</i>-pyrazol-3-yl]-carbamic acid phenyl ester [ No CAS ]
[ 159974-63-7 ]
2-{4-[5-(4-chloro-phenyl)-2<i>H</i>-pyrazol-3-ylcarbamoyl]-piperazin-1-yl}-benzoic acid methyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 7501 - 7511

5
[ 159974-63-7 ]
[ 179480-81-0 ]

Yield	Reaction Conditions	Operation in experiment
20%	With methanol; ammonia; at 0 - 50℃;	1 equiv of 29.232 was dissolved in MeOH (anhydrous) and cooled to 0 C. in a ice-bath in Parr bomb then ammonia gas was bubbled into mixture until saturated. This mixture was then heated to 50 C. in an oil-bath overnight. Materil was concentrated and purified by silica column using 20%MeOH in CHC13 as eluent which resulted in an off-white solid (20% yield) and recovered starting materil. MS (ES) 206 [MH+], tR (method B)=4.14 min.

Reference： [1]Patent: US2003/229067,2003,A1 .Location in patent: Page 31

6
[ 159974-63-7 ]
[ 446831-27-2 ]

Reference： [1]Patent: WO2004/48321,2004,A1 .Location in patent: Page/Page column 55

7
[ 110-85-0 ]
[ 610-94-6 ]
[ 584-08-7 ]
[ 159974-63-7 ]

Yield	Reaction Conditions	Operation in experiment
26%	In 1,4-dioxane; sodium hydroxide;	a. 1-(2-Carbomethoxyphenyl)-piperazine To a solution of methyl 2-bromobenzoate (1.63 g, 17.8 mmol) in 1,4-dioxane (100 ml) at room temperature, were added piperazine (15.3 g, 178 mmol) and K2 CO3 (4.92 g, 35 mmol). The resulting mixture was heated to reflux for 7 days after which the reaction mixture was cooled to room temperature and the solvent and the excess piperazine were removed in vacuo and heating with a hot water bath. The residue was dissolved in 1N NaOH solution and extracted with CH2 Cl2 (6*30 ml), dried over Na2 SO4. The solvent was removed in vacuo to obtain 1-(2-carbomethoxyphenyl)-piperazine as a yellow oil (1.0 g, 26%).

Reference： [1]Patent: US6159990,2000,A

8
[ 110-85-0 ]
[ 610-94-6 ]
[ 159974-63-7 ]

Yield	Reaction Conditions	Operation in experiment
26%	With potassium carbonate; In 1,2-dioxacyclohexane; sodium hydroxide;	a. 1-(2-carbomethoxyphenyl)-piperazine To a solution of methyl 2-bromobenzoate (1.63 g, 17.8 mmol) in 1,6-dioxane (100 ml) at room temperature was added piperazine (15.3 g, 178 mmol) and K2CO3 (4.92 g, 35 mmol). The resulting mixture was heated to reflux for 7 days after which the reaction mixture was cooled to room temperature. The solvent and the excess piperazine were removed in vacuo along with heating with a hot water bath. The residue was dissolved in 1N NaOH solution, extracted with CH2Cl2 (6*30 ml), and dried over Na2SO4. The solvent was removed in vacuo to obtain 1-(2-carbomethoxyphenyl)-piperazine as a yellow oil (1.0 g, 26%).

Reference： [1]Patent: US6218390,2001,B1

9
[ 2164-34-3 ]
[ 159974-63-7 ]
[ 1227170-16-2 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 150℃; for 2.0h;Microwave irradiation;	EXAMPLE 1: Methyl 2-(4-((2,3-dihydrobenzo[6][l,4]dioxin-2-yl)methyl)piperazin-l- yl)benzoateA mixture of 2-(bromomethyl)-2,3-dihydrobenzo[][l,4]dioxine (0.53 g, 2.406 mmol), methyl 2-(piperazin-l-yl)benzoate (0.55 g, 2.406 mmol) and K2CO3 (0.366 g, 2.647 mmol) in DMF (20 ml) was heated in a microwave reactor at 150 0C for 2 h. Water was added to the cooled mixture, which was then extracted three times with EtOAc. The combined extracts were washed well with water and brine, dried and evaporated to give the crude product, which was purified by flash chromatography (gradient of heptane and EtOAc) to give 0.397 g of the title compound. 1H NMR (CDCl3): delta 2.62-2.82 (m, 6H), 3.05-3.13 (m, 4H), 3.89 (s, 3H), 4.02 (dd, IH), 4.29-4.40 (m, 2H), 6.80-6.92 (m, 4H), 7.02 (dd3 IH), 7.04 (d, IH), 7.41 (dd, IH), 7.73 (d, IH).

Reference： [1]Patent: WO2010/58060,2010,A1 .Location in patent: Page/Page column 20

10
[ 16034-49-4 ]
[ 159974-63-7 ]
[ 1253382-56-7 ]

Yield	Reaction Conditions	Operation in experiment
86%		To a vial containing the 2-piperazin-l-yl-benzoic acid methyl ester (0.667 g, 3.03 mmol) is added a pre-mixed solution containing (3,5-dimethyl-pyrazol-l-yl)-acetic acid (0.428 g, 2.78 mmol) and carbonyl dimidazole (0.567 g, 3.50 mmol). The mixture is stirred overnight and then diluted with 200 mL of EtOAc followed by 200 mL of saturated NH4Cl. The organic phase is washed with 2x200 mL of H2O and 1x200 mL of brine, dried (MgSO4), filtered and concentrated to give 0.849 g of 2-{4-[2-(3,5-dimethyl- pyrazol-l-yl)-acetyl]-piperazin-l-yl} -benzoic acid methyl ester in 86% yield.
	With N-ethyl-N,N-diisopropylamine; 1,1'-carbonyldiimidazole; In N,N-dimethyl-formamide; at 20℃;	To a vial containing the 2-piperazin-l-yl-benzoic acid methyl ester (0.667 g, 3.03 mmol) is added a pre-mixed solution containing (3,5-dimethyl-pyrazol-l-yl)-acetic acid (0.428 g, 2.78 mmol) and carbonyl diimidazole (0.567 g, 3.50 mmol). The mixture is stirred overnight and then diluted with 200 mL of EtOAc followed by 200 mL of sat. NH4Cl. The organic phase is washed with 2 x 200 mL of H2O and 1 x 200 mL of brine. The organic phase is dried with MgSO4, filtered and concentrated to give 0.849 g of 2-{4-[2- (3,5-dimethyl-pyrazol-l-yl)-acetyl]-piperazin-l-yl} -benzoic acid methyl ester.

Reference： [1]Patent: WO2010/126851,2010,A1 .Location in patent: Page/Page column 87
[2]Patent: WO2010/126811,2010,A1 .Location in patent: Page/Page column 142-143

11
[ 67-56-1 ]
[ 446831-27-2 ]
[ 159974-63-7 ]

Yield	Reaction Conditions	Operation in experiment
63%		Example 2: Synthesis of 2-{4-[2-(3,5-Dimethyl-pyrazol-l-yl)-acetyl]-piperazin-l-yl}- N-pyridin-4-yl-benzamidee 1 h 16h 2-Piperazin-l-yl-benzoic acid (1.000 g, 4.89 mmol) is suspended in 10 niL of MeOH. To this is added 5 niL of cone. H2SO4. The mixture is stirred for 16 h resulting in a white precipitate. An additional 5 rnL of H2SO4 is added with an additional 10 rnL of MeOH. The reaction volume is increased by an additional 200 mL of MeOH and 60 mL of H2SO4 and the mixture is stirred an additional 2 h and then heated at reflux for 12 h. The reaction volume is then reduced to approximately 175 mL and applied to an ion exchange column, eluting with 5x200 mL of 10% NH3/Me0H and then the product fractions are concentrated. The eluent is co-evaporated with toluene to remove residual water to give 0.667 g of 2-piperazin-l-yl -benzoic acid methyl ester in 63% yield.
		2-Piperazin-l-yl-benzoic acid (1.00 g, 4.89 mmol) is suspended in 10 mL of MeOH.. To this is added 5 mL of cone. H2SO4. The mixture is stirred for 16 h resulting in a white precipitate. The reaction volume is increased by an additional 210 rnL of MeOH and 65 rnL of H2SO4. The mixture stirred for 2 h at room temperature and then heated at reflux for 12 h. The reaction volume is concentrated to approximately 175 mL and applied to an ion exchange column, eluting with 5 x 200 mL of 10% NH3/Me0H. The product fractions are concentrated and then co-evaporated with toluene to remove residual water providing 0.667 g of 2-piperazin-l-yl-benzoic acid methyl ester.

Reference： [1]Patent: WO2010/126851,2010,A1 .Location in patent: Page/Page column 86
[2]Patent: WO2010/126811,2010,A1 .Location in patent: Page/Page column 142-143

12
C₁₈H₁₉N₃O₆S [ No CAS ]
[ 159974-63-7 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 7451 - 7453

13
C₂₁H₃₁N₅O [ No CAS ]
[ 530-62-1 ]
[ 159974-63-7 ]
C₃₄H₄₅N₇O₄ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 1229 - 1232

14
[ 159974-63-7 ]
[ 1253382-57-8 ]

Reference： [1]Patent: WO2010/126851,2010,A1
[2]Patent: WO2010/126811,2010,A1

15
[ 159974-63-7 ]
[ 1253382-55-6 ]

Reference： [1]Patent: WO2010/126851,2010,A1

16
[ 159974-63-7 ]
[ 1253936-85-4 ]

Reference： [1]Patent: WO2010/126811,2010,A1

17
[ 159974-63-7 ]
[ 1253382-59-0 ]

Reference： [1]Patent: WO2010/126811,2010,A1

18
2-(5-amino-2-(furan-2-yl)-7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-7-yl)-2-(2-fluorophenyl)propanoic acid [ No CAS ]
[ 159974-63-7 ]
methyl 2-(4-(2-(5-amino-2-(furan-2-yl)-7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-7-yl)-2-phenylpropanoyl)piperazin-1-yl)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79.2%	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃;	A mixture of 2- (5-amino-2- (furan-2-yl) -7H-pyrazolo [4, 3-e] [1, 2, 4] triazolo [1, 5-c] pyrimidin-7-yl) -2- (2-fluorophenyl) propanoic acid (500 mg, 1.285 mmol) , methyl 2- (piperazin-1-yl) benzoate (424 mg, 1.928 mmol) , HATU (977 mg, 2.571 mmol) , DIPEA (497 mg, 3.856 mmol) in DMF (5 mL) was stirred at rt overnight. The reaction mixture was poured into H2O (5 mL) and extracted with EtOAc (5 mL x 3) . The combined organic layers were washed with brine, dried over Na2SO4, concentrated and purified by column chromatography (DCM/MeOH =40: 1 10: 1) to give the product (603 mg, 79.2%) as white solid. MS: M/e 592 (M+1)+.

Reference： [1]Patent: WO2020/20097,2020,A1 .Location in patent: Paragraph 0756-0758

19
[ 159974-63-7 ]
2-(4-(2-(5-amino-2-(furan-2-yl)-7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-7-yl)-2-phenylpropanoyl)piperazin-1-yl)benzoic acid [ No CAS ]