[ CAS No. 72934-37-3 ]

Name: 72934-37-3|1-(4-Chlorophenyl)cyclopropanecarboxylic acid|95%
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Quality Control of [ 72934-37-3 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 72934-37-3 ]

Product Details of [ 72934-37-3 ]

CAS No. :	72934-37-3	MDL No. :	MFCD00001289
Formula :	C₁₀H₉ClO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YAHLWSGIQJATGG-UHFFFAOYSA-N
M.W :	196.63	Pubchem ID :	98606
Synonyms :

Calculated chemistry of [ 72934-37-3 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.3
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	50.38
TPSA :	37.3 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) :	-5.82 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.91
Log Po/w (XLOGP3) :	2.36
Log Po/w (WLOGP) :	2.39
Log Po/w (MLOGP) :	2.45
Log Po/w (SILICOS-IT) :	2.87
Consensus Log Po/w :	2.4

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.76
Solubility :	0.345 mg/ml ; 0.00176 mol/l
Class :	Soluble
Log S (Ali) :	-2.78
Solubility :	0.324 mg/ml ; 0.00165 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.21
Solubility :	0.121 mg/ml ; 0.000617 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.38

Safety of [ 72934-37-3 ]

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

Application In Synthesis of [ 72934-37-3 ]

* 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 [ 72934-37-3 ]
Downstream synthetic route of [ 72934-37-3 ]

[ 72934-37-3 ] Synthesis Path-Upstream 1~2

1
[ 64399-27-5 ]
[ 72934-37-3 ]

Yield	Reaction Conditions	Operation in experiment
95%	Reflux	The cyclopropanecarbonitrile ( 18 gm) obtained in example 1 was added to 20percent sulfuric acid (184ml). The temperature of the reaction mass was slowly raised and maintained at reflux for 10-12 hours. After 12 hours , ethyl acetate was used to extract the product. The acid product from the organic layer was then extracted into 20percent NaOH solution. The aqueous layer was then acidified to pH 2-4 with concentrated HCl. The white solid product obtained was filtered and washed with water. The product p- chlorophenylcyclopropanecarboxylic acid was dried. The yield was 90-95percent and the product had apurity of 99.4percent by HPLC. The melting point was 152-155⁰C.
90.3%	With sodium hydroxide In water; diethylene glycol for 18 h; Reflux	A stirred solution of 1-(4-chlorophenyl)cyclopropane-1-carbonitrile (step 1, 30.0 g, 169.49 mmol, 1.0 eq), sodium hydroxide (20.3 g, 508.47 mmol, 3.0 eq), diethylene glycol(120 ml) and water (35.4 ml) was refluxed for about 18 hours. TLC indicated startingmaterial was consumed and the desired product was observed. The reaction mixture was poured into water (1800 ml) and acidified to pH4.0 with concentrated HC1 (54 ml). The generated crystals were collected by filtration and dried under vacuum to obtain the desired product (30.0 g, 90.3percent yield) as a pale-brown colour solid. ‘H NMR (300 MHz, DMSO-d6):ppm 12.40 (br.s., 1H), 7.34 (m, 4H), 1.48-1.42 (m, 2H), 1.16-1.10 (m, 2H).

Reference： [1] Patent: WO2009/150660, 2009, A1, . Location in patent: Page/Page column 16
[2] Patent: WO2016/178092, 2016, A2, . Location in patent: Page/Page column 63; 64
[3] Patent: WO2017/64628, 2017, A1, . Location in patent: Page/Page column 33; 34
[4] Chemische Berichte, 1979, vol. 112, p. 3914 - 3933
[5] Patent: US2009/312558, 2009, A1, . Location in patent: Page/Page column 6
[6] Journal of the American Chemical Society, 2011, vol. 133, # 49, p. 19598 - 19601
[7] Organic Letters, 2014, vol. 16, # 24, p. 6314 - 6317
[8] Journal of the American Chemical Society, 2018, vol. 140, # 21, p. 6545 - 6549
[9] Advanced Synthesis and Catalysis, 2018, vol. 360, # 22, p. 4306 - 4311

2
[ 140-53-4 ]
[ 72934-37-3 ]

Reference： [1] Chemische Berichte, 1979, vol. 112, p. 3914 - 3933
[2] Journal of the American Chemical Society, 2011, vol. 133, # 49, p. 19598 - 19601
[3] Patent: WO2016/178092, 2016, A2,
[4] Patent: WO2017/64628, 2017, A1,
[5] Journal of the American Chemical Society, 2018, vol. 140, # 21, p. 6545 - 6549
[6] Advanced Synthesis and Catalysis, 2018, vol. 360, # 22, p. 4306 - 4311

[ 72934-37-3 ] Synthesis Path-Downstream 1~68

1
[ 64399-27-5 ]
[ 72934-37-3 ]

Yield	Reaction Conditions	Operation in experiment
95%	With sulfuric acid; water;Reflux;	The cyclopropanecarbonitrile ( 18 gm) obtained in example 1 was added to 20% sulfuric acid (184ml). The temperature of the reaction mass was slowly raised and maintained at reflux for 10-12 hours. After 12 hours , ethyl acetate was used to extract the product. The acid product from the organic layer was then extracted into 20% NaOH solution. The aqueous layer was then acidified to pH 2-4 with concentrated HCl. The white solid product obtained was filtered and washed with water. The product p- chlorophenylcyclopropanecarboxylic acid was dried. The yield was 90-95% and the product had apurity of 99.4% by HPLC. The melting point was 152-1550C.
90.3%	With sodium hydroxide; In water; diethylene glycol; for 18h;Reflux;	A stirred solution of 1-(4-chlorophenyl)cyclopropane-1-carbonitrile (step 1, 30.0 g, 169.49 mmol, 1.0 eq), sodium hydroxide (20.3 g, 508.47 mmol, 3.0 eq), diethylene glycol(120 ml) and water (35.4 ml) was refluxed for about 18 hours. TLC indicated startingmaterial was consumed and the desired product was observed. The reaction mixture was poured into water (1800 ml) and acidified to pH4.0 with concentrated HC1 (54 ml). The generated crystals were collected by filtration and dried under vacuum to obtain the desired product (30.0 g, 90.3% yield) as a pale-brown colour solid. ?H NMR (300 MHz, DMSO-d6):ppm 12.40 (br.s., 1H), 7.34 (m, 4H), 1.48-1.42 (m, 2H), 1.16-1.10 (m, 2H).
77%	With sodium hydroxide; In methanol; water; at 100 - 105℃; for 14h;Inert atmosphere;	A mixture of nitrile 11 (1.42 g, 8.0 mmol) and NaOH (6.4 g, 160 mmol) in MeOH (40mL) and water (26 mL) was stirred at 100 - 105 C for 14 h under an Ar atmosphere.The mixture was cool down to room temperature and quenched with water, whichwas washed twice with Et2O. 6 M-HCl aq. was added to adjust theseparated water phase to pH = 1. Water phase was extracted twice with AcOEt, and the combinedorganic phase was washed with water, brine, dried (Na 2SO4) and concentrated to give the desiredcarboxylic acid intermediate [4] (1.21g, 77%), which was sufficiently pure without anypurification for the next step.Pale yellow crystals: mp 153 - 155 C [lit.[1] 154 - 156 C];

With sulfuric acid; water;Reflux;

EXAMPLE 2; Preparation of p-chlorophenycyclopropane carboxylic acid; The cyclopropanecarbonitrile (18 gm) obtained in example 1 was added to 20% sulfuric acid (184 ml). The temperature of the reaction mass was slowly raised and maintained at reflux for 10-12 hours. After 12 hours, ethyl acetate was used to extract the product. The acid product from the organic layer was then extracted into 20% NaOH solution. The aqueous layer was then acidified to pH 2-4 with concentrated HCl. The white solid product obtained was filtered and washed with water. The product p-chlorophenylcyclopropanecarboxylic acid was dried. The yield was 90-95% and the product had a purity of 99.4% by HPLC. The melting point was 152-155 C.

Reference： [1]Patent: WO2009/150660,2009,A1 .Location in patent: Page/Page column 16
[2]Patent: WO2016/178092,2016,A2 .Location in patent: Page/Page column 63; 64
[3]Patent: WO2017/64628,2017,A1 .Location in patent: Page/Page column 33; 34
[4]Molecules,2019,vol. 24
[5]Chemische Berichte,1979,vol. 112,p. 3914 - 3933
[6]Patent: US2009/312558,2009,A1 .Location in patent: Page/Page column 6
[7]Journal of the American Chemical Society,2011,vol. 133,p. 19598 - 19601
[8]Organic Letters,2014,vol. 16,p. 6314 - 6317
[9]Journal of the American Chemical Society,2018,vol. 140,p. 6545 - 6549
[10]Advanced Synthesis and Catalysis,2018,vol. 360,p. 4306 - 4311
[11]Journal of the American Chemical Society,2019,vol. 141,p. 10599 - 10604

2
[ 72934-37-3 ]
[ 100-46-9 ]
N-benzyl-3-(4-chlorophenyl)-1-cyclopropanecarboxamide [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1997,vol. 62,p. 2594 - 2603

3
[ 72934-37-3 ]
[ 236418-11-4 ]

Yield	Reaction Conditions	Operation in experiment
95%	With nitric acid; at -30 - -20℃; for 0.25h;	350 ml rauchende Salpetersure werden bei -25 bis -30C portionsweise mit 50.0 g (0.21 Mol) 1-(4-Chlor-phenyl)-cyclopropancarbonsure versetzt. Nach beendeter Zugabe wird noch 15 Minuten bei -25C gerhrt und anschlieend auf Eis gegossen. Die ausgefallene Substanz wird abgesaugt, mit Wasser gewaschen und getrocknet. Ausbeute: 58.5 g (95 % der Theorie), Rf-Wert: 0.43 (Kieselgel; Methylenchlorid/Methanol = 9.5:0.5)
	With nitric acid;	e. 1-(4-Chloro-3-nitrophenyl)-cyclopropanecarboxylic acid 350 ml fuming nitric acid are combined batchwise at -25 to -30 C. with 50.0 g (0.21 mol) of 1-(4-chloro-phenyl)-cyclopropanecarboxylic acid. After it has all been added the mixture is stirred for a further 15 minutes at -25 C. and then poured onto ice. The substance precipitated is suction filtered, washed with water and dried. Yield: 58.5 g (95% of theory), Rf value: 0.43 (silica gel; methylene chloride/methanol=9.5:0.5);
8 g	With nitric acid; at -30℃; for 0.25h;	Step 1): Compound 51 (7.0 g, 35.7 mmol) was added to 50 mL of fuming nitric acid in batches at -30 C. After the addition, the mixture was stirred at -30 C for 15 min.The reaction solution was slowly poured into 100 mL of ice water, filtered, and dried to obtain 8.0 g of the product as a yellow solid (Compound 52).

Reference： [1]Patent: EP1206446,2004,B1 .Location in patent: Page 10-11
[2]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 2297 - 2302
[3]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 3463 - 3468
[4]Patent: US6114532,2000,A
[5]Patent: CN110343089,2019,A .Location in patent: Paragraph 0372-0374; 0375-0376

4
[ 72934-37-3 ]
[ 78682-33-4 ]

Yield	Reaction Conditions	Operation in experiment
	With oxalyl dichloride;N,N-dimethyl-formamide; In dichloromethane; at 0 - 25℃; for 2h;	Step 2.; 1-(4-chlorophenyl)cyclopropanecarbonyl chloride; A catalytic amount of N,N-dimethylformamide (DMF)(10 muL) was added to a mixture of 1-(4-chlorophenyl)cyclopropanecarboxylic acid (1.0 g, 5.1 mmol) and oxalyl chloride (2.2 mL, 25 mmol) in methylene chloride (5 mL) at 0° C. The resulting mixture was stirred at room temperature (about 25° C.) for 2 h. The volatiles were removed under reduced pressure, and the resulting residue was co-evaporated with toluene (2.x.) to provide the crude product, 1-(4-chlorophenyl)cyclopropanecarbonyl chloride, which was used in next step without further purification.
	With oxalyl dichloride;N,N-dimethyl-formamide; In dichloromethane; at 0 - 20℃;Product distribution / selectivity;	A suspension of commercially available 1-(4-chlorophenyl)cyclopropanecarboxylic acid (0.41 g, 2.1 mmol) in DCM (3 mL) was charged with oxalyl chloride (0.35 mL, 4.0 mmol) and N,N-dimethylformamide (5 muL) and stirred 2 h at ambient temperature. The reaction mixture was concentrated under reduced pressure. The resulting acid chloride was diluted with 1,2-dichloroethane (4 mL) and then added to a solution of methyl 6-(3-endo-amino-8-azabicyclo[3.2.1]octan-8-yl)nicotinate (0.18 g, 0.70 mmol), DIEA (0.24 mL, 1.4 mmol) and DMAP (10 mg) in 1,2-dichloroethane (2 mL). After stirring 2 h, the reaction mixture was diluted with EtOAc, washed with satd NaHCO3 and brine, dried (anhyd Na2SO4) and concentrated under reduced pressure. The residue was purified by chromatography (silica, EtOAc/Hex, 20:80 to 75:25) to afford the title compound (0.31 g, quant) as a white solid. 1H NMR (400 MHz, DCM-d2): delta 8.63 (s, 1H); MS (EI): 440 (MH+).; Example 56-[3-endo-({([1-(4-chlorophenyl)cyclopropyl]carbonyl}amino)-8-azabicyclo[3.2.1]oct-8-yl]pyridine-3-carboxamide A solution of commercially available 1-(4-chlorophenyl)-1-cyclopropanecarboxylic acid (7.4 g, 38 mmol) in DCM (75 mL) was chilled to 0° C. and treated with oxalyl chloride (6.6 mL, 76 mmol) and DMF (0.1 mL). The ice-water bath was removed and the reaction mixture was allowed to stir 3 hours at room temperature. The volatiles were removed under reduced pressure and co-evaporated with toluene (2.x.2 mL). The resulting acid chloride was diluted with DCE (40 mL) and added to a cooled (0° C.) solution of ethyl 3-endo-amino-8-azabicyclo[3.2.1]octane-8-carboxylate (5.0 g, 25 mmol) (made by adding ethyl carbonochloridate to the compound from Example 1 (B)), DIEA (8.8 mL, 50 mmol) and DMAP (154 mg, 1.3 mmol) in DCE (85 mL). The ice-water bath was removed and the reaction mixture was allowed to warm to room temperature. After 16 hours, the mixture was diluted with DCM (400 mL), washed with water (100 mL), then dried (anhyd Na2SO4) and filtered. The filtrate was concentrated under reduced pressure to give a residue that was purified by flash chromatography (silica gel, EtOAc/Hex, 50:50 to 80:20) to afford ethyl 3-endo-(1-(4-chlorophenyl)cyclopropane-carboxamido)-8-azabicyclo[3.2.1]octane-8-carboxylate (4.4 g, 42percent) as a yellow crystalline solid. 1H NMR (400 MHz, CDCl3): delta 7.41-7.34 (m, 4H), 5.73 (d, J=7.5 Hz, 1H), 4.23-4.02 (m, 5H), 2.21-1.96 (m, 2H), 1.90-1.81 (m, 2H), 1.62-1.57 (m, 2H), 1.56-1.44 (m, 2H), 1.25-1.09 (m, 5H), 1.05-1.00 (m, 2H).
	With thionyl chloride;N,N-dimethyl-formamide; In toluene; at 20 - 50℃;	1-(4-Chlorophenyl)-cyclopropanecarboxylic acid (2 g, 10.2 mmol) was dissolved in 20 mL dry toluene. Thionyl chloride (2.42 g, 20.4 mmol) was added dropwise at room temperature and a catalytic amount of dry DMF was added. The resultant mixture was stirred at 50 0C for 2 hours. The reaction mixture was concentrated under high vacuum at 60 0C, the residue was dissolved in 10 ml_ DCM and thiosemicarbazide (1.12 g, 10.224 mmol) in a mixture of DMF: DCM (1 :4, 50 ml_) was added at 5-10 0C. The mixture was stirred at room temperature overnight under a nitrogen atmosphere and then the reaction mixture was concentrated under reduced pressure. The residue was dissolved in 200 ml. EtOAc and extracted with water (2x200mL), NaHCO3 (2x200 ml_) and brine (1x200 ml_). After concentration the product was precipitated by petroleum ether to give [[1-(4-chlorophenyl) cyclopropane-carbonyl]amino]thiourea in 32.7 percent yield (900 mg)MS: m/z 270 (M+H) HPLC purity: 99.0percent, NMR (300 MHz, DMSO-d6) delta ppm 1.01 (t, 2 H), 1.1.4 (m, 2H), 7.35 (d, 2 H) 7.45 (d, 2 H).

	With oxalyl dichloride;N,N-dimethyl-formamide; In dichloromethane; for 2h;	Example 392-[1-(4-chlorophenyl)cyclopropyl]-N-[1-oxo-4-(trifluoromethyl)phthalazin-2(1H)-yl]acetamideA solution of 1-(4-chlorophenyl)cyclopropanecarboxylic acid (0.3502 g, 1.781 mmol) and oxalyl dichloride (0.20 mL, 2.293 mmol) in dichloromethane (6 mL) containing a catalytic amount of DMF was stirred for 2 hours, concentrated, and re-dissolved in acetonitrile (5 mL) and THF (5 mL), and cooled to 0° C. A solution of (diazomethyl)trimethylsilane in Et2O (2M, 1.78 mL, 3.56 mmol) was added, stirred for 4 hours, allowing to warm to room temperature, concentrated, diluted with EtOAc, washed with saturated aqueous NaHCO3 and brine, dried (Na2SO4), filtered, and concentrated to give 355 mg of crude product as a dark oil, which was used without purification.A solution of the above crude 1-(1-(4-chlorophenyl)cyclopropyl)-2-diazoethanone (0.050 g, 0.23 mmol), the product from Example 11B (0.0505 g, 0.22 mmol), triethylamine (0.12 mL, 0.86 mmol), and silver benzoate (0.0504 g, 0.220 mmol) in DMF (1 mL) were stirred for 2 hours at 70° C., diluted with EtOAc, washed with saturated aqueous NaHCO3 and brine, dried (Na2SO4), and filtered. The residue was chromatographed on SiO2 (30percent EtOAc/hexanes) to give the title compound (23.0 mg, 0.055 mmol) as a white solid: 1H NMR (300 MHz, DMSO-d6) delta ppm 11.56 (s, 1H), 8.41-8.44 (m, 1H), 7.95-8.20 (m, 3H), 7.22-7.42 (m, 4H), 2.72 (d, J=1.0 Hz, 2H), 1.04-1.10 (m, 2H), 0.84-0.90 (m, 2H); MS (ESI+) M/Z 422 (M+H)+, 439 (M+NH4)+.
	With thionyl chloride; In dichloromethane; at 50℃; for 1h;Inert atmosphere;	General procedure: Thionyl chloride (4 eq) was added dropwise to an oven dried round bottomed flask containingcommercially available acid 1a-f (0.212 mmol ? 29.0 mmol) and dichloromethane (0.3 M). The reactionwas stirred at 50 °C for one hour. The resulting solution was concentrated under vacuum and redissolvedin dichloromethane (20 mL, 0.11 M) and added dropwise to a round bottom flask at 0 °C containing 4-piperidone (1.26 eq), triethylamine (7.5 eq), and THF (0.06 M). After 15 minutes the solution wasrefluxed at 50 °C for 24 hours. The reaction was carefully quenched with saturated aqueous ammoniumchloride and extracted with chloroform (3 x 20 mL). The resultant organic layers were combined anddried over Na2SO4, decanted and concentrated under vacuum. Product purification was achieved by silicagel flash chromatography (40percent ethyl acetate/60percent hexane).
	With thionyl chloride;N,N-dimethyl-formamide; In dichloromethane; at 20℃; for 0.5h;	CM. l-(4-chlorophenyl)-N-(5-methyl-6-(5-methyl-6-oxo-L6-dihvdropyridin-3- yl)pyridin-2-yl)cvclopropanecarboxamide; Step a: 1 -(4-chlorophenyl)-eta-(5-methyl-6-(5-methyl-6-oxo- 1 ,6-dhydropyridin-i- yl)pyridin-2-yl)cyclopropanecarboxamide; To a solution of l-(4-chlorophenyl)cyclopropanecarboxylic acid (39.3 mg, 0.2 mmol) in dichloromethane (2 mL) was added thionyl chloride (43.8 muL, 0.6 mmol) followed by DMF (1 drop) and the reaction was stirred at room temperature for 30 minutes and then the solvent was removed. Toluene (~ ImL) was added, mixed with the residue and then removed by evaporation. The residue was then dissolved in dichloromethane (1 mL) and a solution of 6'- methoxy-3,5'-dimethyl-2,3'-bipyridin-6-amine (46mg, 0.2 mmol) and triethyl amine (83.6 muL, 0.60 mmol) in dichloromethane (1 mL) was added. The reaction was stirred at room temperature for 12 hurs. The reaction was then concentrated. The residue was dissolved in DMSO and purified by reverse phase HPLC (10-99percent acetonitrile/water) to yield 62mg of the product. ESI-MS m/z calc. 407.1, found 408.2 (M+l)+. Retention time 2.07 minutes.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 6213 - 6218
[2]Patent: US2007/270424,2007,A1 .Location in patent: Page/Page column 20
[3]Patent: US2009/247515,2009,A1 .Location in patent: Page/Page column 171-172; 180-181
[4]Patent: WO2010/73011,2010,A2 .Location in patent: Page/Page column 85
[5]Journal of Medicinal Chemistry,2010,vol. 53,p. 6003 - 6017
[6]Journal of Medicinal Chemistry,2010,vol. 53,p. 6003 - 6017
[7]Angewandte Chemie - International Edition,2011,vol. 50,p. 314 - 318
[8]Patent: US2011/124642,2011,A1 .Location in patent: Page/Page column 27
[9]Journal of the American Chemical Society,2011,vol. 133,p. 19598 - 19601
[10]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 1827 - 1830
[11]eLife,2017,vol. 6
[12]Journal of Medicinal Chemistry,2018,vol. 61,p. 84 - 97
[13]Patent: WO2008/141119,2008,A2 .Location in patent: Page/Page column 160

5
[ 72934-37-3 ]
[ 41324-66-7 ]
N-isobutoxycarbonyl-2-isobutoxy-1,2-dihydroquinolin-6-yloxy-Merrifield resin [ No CAS ]
(S)-1-[1-(4-chlorophenyl)-cyclopropanecarbonyl]-pyrrolidine-2-carboxylic acid benzyl ester [ No CAS ]
[ 96847-85-7 ]

Reference： [1]Tetrahedron,2007,vol. 63,p. 8855 - 8871

6
[ 72934-37-3 ]
[ 872421-40-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 6213 - 6218

7
[ 72934-37-3 ]
[ 916923-30-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 6213 - 6218

8
[ 72934-37-3 ]
[ 916923-29-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 6213 - 6218

9
[ 72934-37-3 ]
[ 900505-08-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 3463 - 3468

10
[ 72934-37-3 ]
[ 900504-93-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 3463 - 3468

11
[ 72934-37-3 ]
4-[1-(4-chloro-3-nitro-phenyl)-cyclopropyl]-3-(4-chloro-phenyl)-7-iodo-3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 3463 - 3468

12
[ 72934-37-3 ]
4-[1-(3-amino-4-chloro-phenyl)-cyclopropyl]-3-(4-chloro-phenyl)-7-iodo-1-(2-morpholin-4-yl-ethyl)-3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 3463 - 3468

13
[ 72934-37-3 ]
4-[1-(4-chloro-3-nitro-phenyl)-cyclopropyl]-3-(4-chloro-phenyl)-7-iodo-1-(2-morpholin-4-yl-ethyl)-3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 3463 - 3468

14
[ 72934-37-3 ]
(2-[1-(4-chloro-3-nitro-phenyl)-cyclopropyl]-[(4-chloro-phenyl)-(cyclohex-1-enylcarbamoyl)-methyl]-carbamoyl}-4-iodo-phenyl)-carbamic acid tert-butyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 3463 - 3468

15
[ 72934-37-3 ]
[ 236418-13-6 ]