[ CAS No. 14062-29-4 ]

Name: 14062-29-4|Ethyl 2-(3-chlorophenyl)acetate|98%
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COA NMR CNMR HPLC LC-MS

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Product Details of [ 14062-29-4 ]

CAS No. :	14062-29-4	MDL No. :	MFCD07787498
Formula :	C₁₀H₁₁ClO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	198.65	Pubchem ID :	-
Synonyms :

Calculated chemistry of [ 14062-29-4 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.3
Num. rotatable bonds :	4
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	52.12
TPSA :	26.3 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.54 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.61
Log Po/w (XLOGP3) :	2.78
Log Po/w (WLOGP) :	2.45
Log Po/w (MLOGP) :	2.84
Log Po/w (SILICOS-IT) :	3.03
Consensus Log Po/w :	2.74

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.9
Solubility :	0.25 mg/ml ; 0.00126 mol/l
Class :	Soluble
Log S (Ali) :	-2.99
Solubility :	0.204 mg/ml ; 0.00103 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.9
Solubility :	0.0248 mg/ml ; 0.000125 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.64

Safety of [ 14062-29-4 ]

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

Application In Synthesis of [ 14062-29-4 ]

* 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 [ 14062-29-4 ]
Downstream synthetic route of [ 14062-29-4 ]

[ 14062-29-4 ] Synthesis Path-Upstream 1~1

1
[ 623-73-4 ]
[ 108-90-7 ]
[ 14062-24-9 ]
[ 40061-54-9 ]
[ 14062-29-4 ]

Reference： [1] Organometallics, 2017, vol. 36, # 1, p. 172 - 179

[ 14062-29-4 ] Synthesis Path-Downstream 1~68

1
[ 64-17-5 ]
[ 1529-41-5 ]
[ 14062-29-4 ]

Reference： [1]Journal of the Chemical Society,1954,p. 3263,3268

2
[ 4360-47-8 ]
[ 14062-29-4 ]
[ 134823-34-0 ]
[ 134823-34-0 ]

Reference： [1]European Journal of Medicinal Chemistry,1991,vol. 26,p. 19 - 32
[2]European Journal of Medicinal Chemistry,1991,vol. 26,p. 19 - 32

3
[ 103-36-6 ]
[ 58357-84-9 ]
[ 621-79-4 ]
[ 14062-29-4 ]
[ 77418-76-9 ]

Reference： [1]Journal of Heterocyclic Chemistry,1980,vol. 17,p. 1605 - 1607

4
[ 64-17-5 ]
[ 7023-78-1 ]
[ 14062-29-4 ]

Reference： [1]Journal of Organometallic Chemistry,1991,vol. 409,p. 385 - 409

5
[ 6048-06-2 ]
[ 58357-84-9 ]
[ 14062-29-4 ]
[ 18166-64-8 ]
[ 77418-81-6 ]

Reference： [1]Journal of Heterocyclic Chemistry,1980,vol. 17,p. 1605 - 1607

6
[ 14062-29-4 ]
[ 41024-33-3 ]

Reference： [1]Journal of Medicinal Chemistry,1981,vol. 24,p. 481 - 490
[2]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 3535 - 3539
[3]Organic Letters,2018,vol. 20,p. 1832 - 1836

7
[ 20511-20-0 ]
[ 58357-84-9 ]
[ 14062-29-4 ]
[ 18254-00-7 ]
[ 77418-86-1 ]

Reference： [1]Journal of Heterocyclic Chemistry,1980,vol. 17,p. 1605 - 1607

8
[ 14062-29-4 ]
[ 67-64-1 ]
[ 82129-59-7 ]

Reference： [1]Heterocycles,1983,vol. 20,p. 2189 - 2195

9
[ 894421-72-8 ]
[ 14062-29-4 ]
3-(1-benzyl-5-p-tolyl-1H-pyrazol-3-yl)-2-(3-chloro-phenyl)-propionic acid ethyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 72 - 76

10
[ 894421-51-3 ]
[ 14062-29-4 ]
2-(3-chloro-phenyl)-3-(1,5-di-p-tolyl-1H-pyrazol-3-yl)-propionic acid ethyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 72 - 76

11
[ 894421-67-1 ]
[ 14062-29-4 ]
2-(3-chloro-phenyl)-3-[1-(4-chloro-phenyl)-5-p-tolyl-1H-pyrazol-3-yl]-propionic acid ethyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 72 - 76

12
[ 894421-68-2 ]
[ 14062-29-4 ]
2-(3-chloro-phenyl)-3-[1-(3-chloro-phenyl)-5-p-tolyl-1H-pyrazol-3-yl]-propionic acid ethyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 72 - 76

13
[ 894419-56-8 ]
[ 14062-29-4 ]
2-(3-chloro-phenyl)-3-[5-(2-chloro-phenyl)-1-(4-methoxy-phenyl)-1H-pyrazol-3-yl]-propionic acid ethyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 72 - 76

14
[ 894419-58-0 ]
[ 14062-29-4 ]
3-[1,5-bis-(4-methoxy-phenyl)-1H-pyrazol-3-yl]-2-(3-chloro-phenyl)-propionic acid ethyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 72 - 76

15
[ 828918-70-3 ]
[ 14062-29-4 ]
2-(3-chloro-phenyl)-3-[1-(3,4-dichloro-phenyl)-5-p-tolyl-1H-pyrazol-3-yl]-propionic acid ethyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 72 - 76

16
[ 648869-73-2 ]
[ 14062-29-4 ]
2-(3-chloro-phenyl)-3-[5-(3,4-dichloro-phenyl)-1-(4-methoxy-phenyl)-1H-pyrazol-3-yl]-propionic acid ethyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 72 - 76

17
[ 894419-59-1 ]
[ 14062-29-4 ]
3-[5-benzo[1,3]dioxol-5-yl-1-(4-methoxy-phenyl)-1H-pyrazol-3-yl]-2-(3-chloro-phenyl)-propionic acid ethyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 72 - 76

18
[ 894421-69-3 ]
[ 14062-29-4 ]
2-(3-chloro-phenyl)-3-[5-p-tolyl-1-(4-trifluoromethyl-phenyl)-1H-pyrazol-3-yl]-propionic acid ethyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 72 - 76

19
[ 894419-43-3 ]
[ 14062-29-4 ]
2-(3-chloro-phenyl)-3-[1-(4-methoxy-phenyl)-5-(4-phenoxy-phenyl)-1H-pyrazol-3-yl]-propionic acid ethyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 72 - 76

20
[ 14062-29-4 ]
[ 119540-36-2 ]
2-(3-chloro-phenyl)-3-[1-(4-methoxy-phenyl)-5-p-tolyl-1H-pyrazol-3-yl]-propionic acid ethyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 72 - 76

21
[ 14062-29-4 ]
[ 119540-35-1 ]
2-(3-chloro-phenyl)-3-[5-(4-chloro-phenyl)-1-(4-methoxy-phenyl)-1H-pyrazol-3-yl]-propionic acid ethyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 72 - 76

22
[ 14062-29-4 ]
[ 781663-78-3 ]
2-(3-chloro-phenyl)-3-[1-(4-methoxy-phenyl)-5-phenyl-1H-pyrazol-3-yl]-propionic acid ethyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 72 - 76

23
[ 100-48-1 ]
[ 14062-29-4 ]
[ 556-61-6 ]
[ 74-88-4 ]
5-(3-chloro-phenyl)-3-methyl-2-methylsulfanyl-6-pyridin-4-yl-3H-pyrimidin-4-one [ No CAS ]

Reference： [1]Tetrahedron,2006,vol. 62,p. 11714 - 11723

24
[ 14062-29-4 ]
[ 105-58-8 ]
[ 93307-66-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 1586 - 1605
[2]Journal of Heterocyclic Chemistry,2012,vol. 49,p. 1415 - 1421

25
[ 14062-29-4 ]
C₃₀H₃₅N₇OCl₂ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 3535 - 3539

26
[ 14062-29-4 ]
[ 946005-77-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 3535 - 3539

27
[ 14062-29-4 ]
[ 946005-78-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 3535 - 3539

28
[ 14062-29-4 ]
[ 926008-51-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 1586 - 1605

29
[ 14062-29-4 ]
[ 146533-36-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 1586 - 1605

30
[ 14062-29-4 ]
[ 926008-67-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 1586 - 1605

31
[ 14062-29-4 ]
C₂₀H₁₇N₄Cl [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 1586 - 1605

32
[ 14062-29-4 ]
3-[1,5-bis-(4-methoxy-phenyl)-1H-pyrazol-3-yl]-2-(3-chloro-phenyl)-propionic acid [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 72 - 76

33
[ 14062-29-4 ]
[ 773851-49-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 4735 - 4739

34
[ 14062-29-4 ]
N-[4-(3-chloro-phenyl)-5-oxo-5H-isoxazol-2-ylmethyl]-acetamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 4735 - 4739

35
[ 14062-29-4 ]
[ 82129-58-6 ]

Reference： [1]Heterocycles,1983,vol. 20,p. 2189 - 2195

36
[ 14062-29-4 ]
(E)-5-(3-Chloro-phenyl)-6-dimethylamino-3-[1-dimethylamino-meth-(E)-ylidene]-hex-5-ene-2,4-dione [ No CAS ]

Reference： [1]Heterocycles,1983,vol. 20,p. 2189 - 2195

37
[ 14062-29-4 ]
[ 86215-14-7 ]

Reference： [1]Journal of Medicinal Chemistry,1981,vol. 24,p. 481 - 490

38
[ 14062-29-4 ]
[ 66503-98-8 ]

Reference： [1]Journal of Medicinal Chemistry,1981,vol. 24,p. 481 - 490

39
[ 14062-29-4 ]
[ 66503-97-7 ]

Reference： [1]Journal of Medicinal Chemistry,1981,vol. 24,p. 481 - 490

40
[ 14062-29-4 ]
[ 66503-96-6 ]

Reference： [1]Journal of Medicinal Chemistry,1981,vol. 24,p. 481 - 490

41
[ 618-46-2 ]
[ 14062-29-4 ]

Reference： [1]Journal of Organometallic Chemistry,1991,vol. 409,p. 385 - 409

42
[ 792953-05-0 ]
[ 14062-29-4 ]
6-(3-chlorobenzyl)-1-(2,6-dimethylphenyl)-1,5-dihydropyrazolo[3,4-d]pyrimidin-4-one [ No CAS ]

Reference： [1]Patent: WO2004/99210,2004,A1 .Location in patent: Page/Page column 42

43
[ 792953-06-1 ]
[ 14062-29-4 ]
6-(3-chlorobenzyl)-1-(2,3-dimethylphenyl)-1,5-dihydropyrazolo[3,4-d]pyrimidin-4-one [ No CAS ]

Reference： [1]Patent: WO2004/99210,2004,A1 .Location in patent: Page/Page column 43

44
[ 666235-33-2 ]
[ 14062-29-4 ]
6-(3-chlorobenzyl)-1-cyclopentyl-1,5-dihydro-4H-pyrazolo[3,4-d]-pyrimidin-4-one [ No CAS ]

Reference： [1]Patent: WO2004/18474,2004,A1 .Location in patent: Page/Page column 32

45
[ 14062-29-4 ]
[ 95-92-1 ]
[ 1101067-21-3 ]

Yield	Reaction Conditions	Operation in experiment
		Part A: Diethyl 2-oxo-3-(3-chlorophenyl)succinate. This compound is prepared according to the method of Klioze and Ehrgott (U.S. Pat. No. 4,216,218) from diethyl oxalate and ethyl (3-chlorophenyl)acetate.

Reference： [1]Patent: US2003/73733,2003,A1

46
[ 27935-87-1 ]
[ 14062-29-4 ]
ammonium chloride [ No CAS ]
[ 300355-00-4 ]

Yield	Reaction Conditions	Operation in experiment
93%	In N,N,N,N,N,N-hexamethylphosphoric triamide;	A solution of freshly prepared lithium diisopropylamide (23 mL of 0.31M stock solution, 7.13 mmol) cooled to -78 C. was treated with <strong>[14062-29-4](3-chloro-phenyl)-acetic acid ethyl ester</strong> (1.28 g, 6.48 mmol) in tetrahydrofiran/hexamethylphosphoramide (16.1 mL, 3:1). The resulting solution was stirred at -78 C. for 45 min. At this time, the reaction was treated with a solution of iodomethylcyclopentane (1.50 g, 7.13 mmol) in hexamethylphosphoramide (1 mL). The reaction mixture was stirred at -78 C. for 4 h. The reaction was warmed to 25 C. and stirred at 25 C. for 16 h. The reaction mixture was then quenched by the dropwise addition of a saturated aqueous ammonium chloride solution (20 mL). This mixture was poured into water (100 mL) and extracted with ethyl acetate (3*50 mL). The organics were dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 75/25 hexanes/ethyl acetate) afforded 2-(3-chloro-phenyl)-3-cyclopentyl-propionic acid ethyl ester (1.70 g, 93%) as a yellow oil: EI-HRMS m/e calcd for C16H21ClO2 (M+) 280.1230, found 280.1238.
93%	In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide;	A solution of freshly prepared lithium diisopropylamide (23 mL of 0.31 M stock solution, 7.13 mmol) cooled to -78 C. was treated with <strong>[14062-29-4](3-chloro-phenyl)-acetic acid ethyl ester</strong> (1.28 g, 6.48 mmol) in tetrahydrofuran/hexamethylphosphoramide (16.1 mL, 3:1). The resulting solution was stirred at -78 C. for 45 min. At this time, the reaction was treated with a solution of iodomethylcyclopentane (1.50 g, 7.13 mmol) in hexamethylphosphoramide (1 mL). The reaction mixture was stirred at -78 C. for 4 h. The reaction was warmed to 25 C. and stirred at 25 C. for 16 h. The reaction mixture was then quenched by the dropwise addition of a saturated aqueous ammonium chloride solution (20 mL). This mixture was poured into water (100 mL) and extracted with ethyl acetate (3*50 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 75/25 hexanes/ethyl acetate) afforded 2-(3-chloro-phenyl)-3-cyclopentyl-propionic acid ethyl ester (1.70 g, 93%) as a yellow oil: EI-HRMS m/e calcd for C16H21ClO2 (M+) 280.1230, found 280.1238.

Reference： [1]Patent: US2001/39344,2001,A1
[2]Patent: US6610846,2003,B1

47
2-dimethylamino-1-methyl-1-pyrrolinium-methylsulfate [ No CAS ]
[ 14062-29-4 ]
2-(α-ethoxycarbonyl-3-chlorobenzylidene)-1-methylpyrrolidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium; In ethanol;	EXAMPLE 36 2-(alpha-ethoxycarbonyl-3-chlorobenzylidene)-1-methylpyrrolidine Follow the procedure of Example 31 to obtain 70 g (90% of theory) of the title compound (b.p. 137 at 0.006 mm of Hg) from 91 g of 2-dimethylamino-1-methyl-1-pyrrolinium-methylsulfate, 55.1 g of <strong>[14062-29-4]3-chlorophenylacetic acid ethyl ester</strong> and a solution of 8.8 g of sodium in 175 ml of ethanol.

Reference： [1]Patent: US4279918,1981,A

48
[ 14062-24-9 ]
[ 614-18-6 ]
[ 14062-29-4 ]
[ 40061-24-3 ]

Yield	Reaction Conditions	Operation in experiment
		p-xylyl-(3-pyridyl)-ketone, m.p. 90-91C (from ether), starting from 21.0 g of p-tolylacetic acid ethyl ester and 17.8 g of nicotinic acid ethyl ester; m-chlorobenzyl-(3-pyridyl)-ketone, m.p. 65-67C, starting from 25.0 g of m-chlorophenylacetic acid ethyl ester and 19.0 g of nicotinic acid ethyl ester; p-chlorobenzyl-(3-pyridyl)-ketone (oil), starting from 25.0 g of p-chlorophenylacetic acid ethyl ester and 19.0 g of nicotinic acid ethyl ester; p-methoxybenzyl(4-pyridyl)-ketone, m.p. 130-132C, starting from 25.2 g of p-methoxyphenylacetic acid ethyl ester and 18.9 g of nicotinic acid ethyl ester; m-methoxybenzyl-(3-pyridyl)-ketone, b.p. 160-165C/0.05 Torr, starting from 25.2 g of m-methoxyphenylacetic acid ethyl ester and 19.0 g of nicotinic acid ethyl ester.

Reference： [1]Patent: US3940486,1976,A

49
[ 630107-81-2 ]
[ 14062-29-4 ]
6-(3-chlorobenzyl)-1-(2-fluorophenyl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 20 6-(3-Chlorobenzyl)-1-(2-fluorophenyl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one In analogy to the preparation of Example 9, 171 mg (73% of theory) of the desired product are obtained as a colourless solid starting from 0.15 g (0.66 mmol) of 5-amino-1-(2-fluorophenyl)-1H-pyrazole-4-carboxamide (Example 28A), 0.405 g (98% purity, 1.99 mmol) of ethyl (3-chlorophenyl)acetate and 0.132 g (3.32 mmol) of 60% sodium hydride. m.p.: 197 C. MS (ESI pos): m/z=355 (M+H)+ 1H-NMR (300 MHz, DMSO-d6):delta=3.95 (s, 2H), 7.2-7.7 (m, 8H), 8.3 (s, 1H), 12.5 (s, 1H) ppm.

Reference： [1]Patent: US2007/161662,2007,A1

50
[ 792953-11-8 ]
[ 14062-29-4 ]
6-(3-chlorobenzyl)-1-(2-methylphenyl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 16 6-(3-Chlorobenzyl)-1-(2-methylphenyl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one In analogy to the preparation of Example 9, 146 mg (60% of theory) of the desired product are obtained as a colourless solid starting from 0.15 g (0.69 mmol) of 5-amino-1-(2-methylphenyl)-1H-pyrazole-4-carboxamide (Example 25A), 0.482 g (2.43 mmol) of ethyl (3-chlorophenyl)acetate and 0.139 g (3.47 mmol) of 60% sodium hydride. m.p.: 215 C. MS (ESI pos): m/z=351 (M+H)+ 1H-NMR (300 MHz, DMSO-d6): delta=2.05 (s, 3H), 3.9 (s, 2H), 7.2-7.5 (m, 8H), 8.25 (s, 1H), 12.5 (s, 1H) ppm.

Reference： [1]Patent: US2007/161662,2007,A1

51
[ 792953-12-9 ]
[ 14062-29-4 ]
6-(3-chlorobenzyl)-1-(2-ethylphenyl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 18 6-(3-Chlorobenzyl)-1-(2-ethylphenyl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one In analogy to the preparation of Example 9, 65 mg (27% of theory) of the desired product are obtained as a colourless solid starting from 0.15 g (0.65 mmol) of 5-amino-1-(2-ethylphenyl)-1H-pyrazole-4-carboxamide (Example 26A), 0.398 g (1.95 mmol) of ethyl (3-chlorophenyl)acetate and 0.130 g (3.26 mmol) of 60% sodium hydride. m.p.: 208 C. MS (ESI pos): m/z=365 (M+H)+ 1H-NMR (300 MHz, DMSO-d6): delta=0.9 (t, 3H), 2.35 (q, 2H), 3.9 (s, 2H), 7.15-7.5 (m, 8H), 8.25 (s, 1H), 12.45 (s, 1H) ppm.

Reference： [1]Patent: US2007/161662,2007,A1

52
[ 792953-13-0 ]
[ 14062-29-4 ]
6-(3-chlorobenzyl)-1-(2-trifluoromethylphenyl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 19 6-(3-Chlorobenzyl)-1-(2-trifluoromethylphenyl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one In analogy to the preparation of Example 9, 157 mg (70% of theory) of the desired product are obtained as a colourless solid starting from 0.15 g (0.56 mmol) of 5-amino-1-(2-trifluoromethylphenyl)-1H-pyrazole-4-carboxamide (Example 27A), 0.339 g (1.67 mmol) of ethyl (3-chlorophenyl)acetate and 0.111 g (2.78 mmol) of 60% sodium hydride. m.p.: 152 C. MS (ESI pos): m/z=405 (M+H)+ 1H-NMR (300 MHz, DMSO-d6): delta=3.9 (s, 2H), 7.15-7.5 (m, 4H), 7.6-8.05 (m, 4H), 8.3 (s, 1H), 12.5 (s, 1H) ppm.

Reference： [1]Patent: US2007/161662,2007,A1

53
[ 792953-14-1 ]
[ 14062-29-4 ]
6-(3-chlorobenzyl)-1-(2-chlorophenyl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 21 6-(3-Chlorobenzyl)-1-(2-chlorophenyl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one In analogy to the preparation of Example 9, 160 mg (70% of theory) of the desired product are obtained as a colourless solid starting from 0.15 g (0.63 mmol) of 5-amino-1-(2-chlorophenyl)-1H-pyrazole-4-carboxamide (Example 29A), 0.387 g (98% purity, 1.90 mmol) of ethyl (3-chlorophenyl)acetate and 0.127 g (3.17 mmol) of 60% sodium hydride. m.p.: 188 C. MS (ESI pos): m/z=372 (M+H)+ 1H-NMR (300 MHz, DMSO-d6): delta=3.9 (s, 2H), 7.2-7.75 (m, 8H), 8.3 (s, 1H), 12.5 (s, 1H) ppm.

Reference： [1]Patent: US2007/161662,2007,A1

54
[ 792953-15-2 ]
[ 14062-29-4 ]
6-(3-chlorobenzyl)-1-(2-pyridinyl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 22 6-(3-Chlorobenzyl)-1-(2-pyridinyl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one In analogy to the preparation of Example 9, 103 mg (41% of theory) of the desired product are obtained as a colourless solid starting from 0.15 g (0.74 mmol) of 5-amino-1-(2-pyridinyl)-1H-pyrazole-4-carboxamide (Example 30A), 0.451 g (98% purity, 2.21 mmol) of ethyl (3-chlorophenyl)acetate and 0.148 g (3.69 mmol) of 60% sodium hydride. m.p.: 230 C. MS (ESI pos): m/z=338 (M+H)+ 1H-NMR (300 MHz, DMSO-d6): delta=4.0 (s, 2H), 7.2-7.75 (m, 5H), 7.9-8.05 (m, 2H), 8.3 (s, 1H), 8.6 (d, 1H), 12.5 (s, 1H) ppm.

Reference： [1]Patent: US2007/161662,2007,A1

55
[ 792953-16-3 ]
[ 14062-29-4 ]
6-(3-chlorobenzyl)-1-(2-methoxyphenyl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 23 6-(3-Chlorobenzyl)-1-(2-methoxyphenyl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one In analogy to the preparation of Example 9, 180 mg (76% of theory) of the desired product are obtained as a colourless solid starting from 0.15 g (0.65 mmol) of 5-amino-1-(2-methoxyphenyl)-1H-pyrazole-4-carboxamide (Example 31A), 0.394 g (98% purity, 1.94 mmol) of ethyl (3-chlorophenyl)acetate and 0.129 g (3.23 mmol) of 60% sodium hydride. m.p.: 196 C. MS (ESI pos): m/z=367 (M+H)+ 1H-NMR (300 MHz, DMSO-d6): delta=3.7 (s, 3H), 3.9 (s, 2H), 7.0-7.6 (m, 8H), 8.2 (s, 1H), 12.4 (s, 1H) ppm.

Reference： [1]Patent: US2007/161662,2007,A1

56
[ 14062-29-4 ]
[ 1093222-12-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 9991 - 10000

57
[ 39557-31-8 ]
[ 14062-29-4 ]
C₁₃H₁₄Cl₂O₂ [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2009,vol. 74,p. 5100 - 5103

58
[ 27935-87-1 ]
[ 14062-29-4 ]
[ 300355-00-4 ]

Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 3618 - 3625

59
[ 14062-29-4 ]
[ 66464-86-6 ]

Reference： [1]Chinese Journal of Chemistry,2010,vol. 28,p. 605 - 612

60
[ 14062-29-4 ]
[ 5736-03-8 ]
C₁₆H₂₁ClO₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of 32.5 mmoles of LDA (prepared by the addition of 20.4 mL of 1.6 molar nBuLi to 4.98 mL of diisopropylamine in 90 mL of THF at 0 C.) was added dropwise a solution of phenyl acetates of formula (3) wherein R1=R2=H, Br, Cl, F and/or methoxy (35.8 mmole) in 20 mL of THF at -78 C. The resulting mixture was stirred at that temperature for 30 minutes followed by the addition of 8 mL of HMPA and stirred for further 20 minutes. To this mixture was added dropwise a solution of aldehyde of formula (2) (5.8 g, 32.5 mmole) in 20 mL of THF and the stirring was continued at -78 C. for 1 h. The reaction mixture was allowed to warm to room temperature followed by quenching with ammonium chloride solution. The reaction mixture was diluted with 100 mL of ethyl acetate, washed with water (2×100 mL), 1 N HCl solution (2×50 mL), water (2×100 mL), dried over Na2SO4 and concentrated. The residue was purified by column chromatography to afford the hydroxy ester of formula (4) as a pale yellow pasty mass. Yield 50-60%.

Reference： [1]Patent: US2007/259948,2007,A1 .Location in patent: Page/Page column 16

61
[ 64-17-5 ]
[ 201230-82-2 ]
[ 108-41-8 ]
[ 14062-29-4 ]

Yield	Reaction Conditions	Operation in experiment
83%	With di-tert-butyl peroxide; dichloro[4,5-bis(diphenylphosphino)-9,9?-dimethylxanthene]palladium(II); at 120℃; under 7600.51 Torr; for 16h;	m-Chlorotoluene (1.89 g), ethanol (46 mg), di-tert-butyl peroxide (73 mg, 1 equivalent), and Pd(Xantphos)Cl2 (3.8 mg, 1 mol %) were added into a reaction kettle, into which 10 atm carbon monoxide was introduced. The reaction was heated to 120 C., and stirred at this constant temperature for 16 h. After the reaction was completed, carbon monoxide was discharged, and 82 mg ethyl m-chlorophenylacetate was obtained by column chromatography, in a yield of 83%. 1HNMR (400 MHz, CDCl3) delta 1.24 (t, J=7.2 Hz, 3H), 3.58 (s, 2H), 4.13 (q, J=7.2 Hz, 2H), 7.15-7.18 (m, 1H), 7.24-7.26 (m, 1H), 7.29 (s, 1H); 13CNMR (100 MHz, CDCl3) delta 14.2, 40.9, 61.1, 127.3, 127.5, 129.5, 129.8, 134.3, 135.9, 170.9; HRMS (ESI) calcd. for C10H11ClNaO2 [M+Na]: 221.0340. found: 221.0342. The ethyl m-chlorophenylacetate obtained was dissolved in 1,4-dioxane. 6 N sodium hydroxide solution was added, and the reaction was heated to 60 C. After 2 h of reaction, the pH value was adjusted to 1 by adding 2 N hydrochloric acid. After removing the organic solvent under reduced pressure, 64 mg product m-chlorophenylacetic acid was obtained by extraction with ethyl acetate, and the yield of hydrolysis was 91%.

Reference： [1]Patent: US2013/303798,2013,A1 .Location in patent: Paragraph 0068; 0069
[2]Journal of the American Chemical Society,2012,vol. 134,p. 9902 - 9905

62
[ 14062-29-4 ]
[ 1398179-38-8 ]

Reference： [1]Chemical Communications,2015,vol. 51,p. 15446 - 15449
[2]Journal of the American Chemical Society,2012,vol. 134,p. 15257 - 15260
[3]Journal of the American Chemical Society,2015,vol. 137,p. 14496 - 14501
[4]Journal of Organic Chemistry,2016,vol. 81,p. 2943 - 2949
[5]Chinese Journal of Chemistry,2016,vol. 34,p. 469 - 472
[6]European Journal of Organic Chemistry,2017,vol. 2017,p. 324 - 331
[7]Organic Letters,2018,vol. 20,p. 4672 - 4676
[8]Journal of Organic Chemistry,2019,vol. 84,p. 4478 - 4485

63
[ 14062-29-4 ]
[ 1398180-90-9 ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 15257 - 15260
[2]European Journal of Organic Chemistry,2017,vol. 2017,p. 324 - 331

64
[ 14062-29-4 ]
[ 1276433-85-2 ]

Reference： [1]Journal of Heterocyclic Chemistry,2012,vol. 49,p. 1415 - 1421

65
[ 14062-29-4 ]
[ 1430852-67-7 ]

Reference： [1]Journal of Heterocyclic Chemistry,2012,vol. 49,p. 1415 - 1421

66
[ 14062-29-4 ]
[ 1430852-70-2 ]

Reference： [1]Journal of Heterocyclic Chemistry,2012,vol. 49,p. 1415 - 1421

67
[ 14062-29-4 ]
[ 1430852-64-4 ]

Reference： [1]Journal of Heterocyclic Chemistry,2012,vol. 49,p. 1415 - 1421

68
[ 14062-29-4 ]
[ 1449391-41-6 ]

Reference： [1]European Journal of Organic Chemistry,2013,p. 4255 - 4261

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[ CAS No. 14062-29-4 ]

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[ 14062-29-4 ] Synthesis Path-Upstream 1~1

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