CAS No.156897-06-2,Licofelone Suppliers

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Basic Information

Molecular Structure:
CAS No.:	156897-06-2
Name:	Licofelone
Article Data:	10

Formula:	C₂₃H₂₂ClNO₂
Molecular Weight:	379.886
Synonyms:	ML 3000;[2,2-Dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl]aceticacid;
EINECS:	694-581-3
Density:	1.23 g/cm³
Melting Point:	162-163 °C
Boiling Point:	539.7 °C at 760 mmHg
Flash Point:	280.2 °C
Appearance:	Yellowish solid
PSA:	42.23000
LogP:	5.68490

Synthetic route

: 156897-35-7
ethyl 2-(6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl)acetate

: 156897-06-2
licofelone

Conditions

Conditions	Yield
With sodium hydroxide In ethanol; water at 80℃;	77%
With sodium hydroxide In ethanol at 80℃; for 0.25h;	77%
With sodium hydroxide In ethanol for 0.166667h; Heating;	75.5%
Stage #1: ethyl 2-(6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl)acetate With sodium hydroxide; water In ethanol for 0.5h; Heating / reflux; Stage #2: With hydrogenchloride In ethanol; water Product distribution / selectivity;	64%
With aq. alkaline hydroxide at 60 - 70℃; for 1h;

: 1061179-20-1
methyl 2-(6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizine-5-yl)acetate

: 156897-06-2
licofelone

Conditions

Conditions	Yield
Stage #1: methyl 2-(6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizine-5-yl)acetate With sodium hydroxide; water In ethanol for 0.5h; Heating / reflux; Stage #2: With hydrogenchloride In ethanol; water Product distribution / selectivity;	71%
With aq. alkaline hydroxide at 60 - 70℃; for 1h;

: 262426-70-0
[6-(4-chlorophenyl)-2,3-dihydro-2,2-dimethyl-7-phenyl-1H-pyrrolizin-5-yl]acetic acid tert-butyl ester

: 156897-06-2
licofelone

Conditions

Conditions	Yield
Stage #1: [6-(4-chlorophenyl)-2,3-dihydro-2,2-dimethyl-7-phenyl-1H-pyrrolizin-5-yl]acetic acid tert-butyl ester With sodium hydroxide; water In ethanol for 8h; Heating / reflux; Stage #2: With hydrogenchloride In ethanol; water Product distribution / selectivity;	60%
With aq. alkaline hydroxide at 60 - 70℃; for 10h;

: C23H20ClNO3

: 156897-06-2
licofelone

Conditions

Conditions	Yield
With hydrazine hydrate; potassium hydroxide In ethylene diglycol at 85 - 145℃; for 7h; Wolff-Kishner reduction;	55%
With hydrazine hydrate; potassium hydroxide In diethylene glycol at 85 - 145℃; for 7h; Wolff-Kishner reduction;	55%
With hydrazine hydrate; potassium hydroxide In diethylene glycol at 50 - 145℃; Wolff-Kishner reduction;	55.6%

: 1061179-22-3
2-(6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizine-5-yl)acetamide

: 156897-06-2
licofelone

Conditions

Conditions	Yield
Stage #1: 2-(6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizine-5-yl)acetamide With sulfuric acid; water In methanol for 4h; Heating / reflux; Stage #2: With sodium hydroxide; water In methanol for 4h; Heating / reflux; Stage #3: With hydrogenchloride In methanol; water Product distribution / selectivity;	50%

: 3355-31-5
1-chloro-3-phenyl-2-propyne

(1,2-dimethyl-3-zirconacyclopent-1-ene)(C5H5)2: (1,2-dimethyl-3-zirconacyclopent-1-ene)(C5H5)2

: 156897-06-2
licofelone

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: 90 percent / aq. NaOH, NaI, n-Bu4NI / toluene / 24 h / 50 °C 2: 1.) Et3N, 2.) NaBH(OAc)3 / 1) CH2Cl2, rt, 15 min; 2) CH2Cl2, rt, 12 h 3: 68 percent / pivalic acid / 5 h / 150 °C 4: 77 percent / EtONa / ethanol / 15 h / Ambient temperature 5: 1.) NaH / 1) THF, rt, 1 h; 2) THF, rt, 12 h 6: 92 percent / Pd(PPh3)4, Na2CO3 / tetrahydrofuran; H2O / 1) rt, 1 h; 2) reflux, 1 h 7: 1.) p-toluenesulfonhydrazide, p-TsOH*H2O, 2.) NaBH3CN / 1) EtOH, reflux, 7 h; 2) EtOH, reflux, 4 h 8: 77 percent / aq. NaOH / ethanol / 0.25 h / 80 °C View Scheme

Yield

Multi-step reaction with 8 steps
1: 90 percent / aq. NaOH, NaI, n-Bu4NI / toluene / 24 h / 50 °C
2: 1.) Et3N, 2.) NaBH(OAc)3 / 1) CH2Cl2, rt, 15 min; 2) CH2Cl2, rt, 12 h
3: 68 percent / pivalic acid / 5 h / 150 °C
4: 77 percent / EtONa / ethanol / 15 h / Ambient temperature
5: 1.) NaH / 1) THF, rt, 1 h; 2) THF, rt, 12 h
6: 92 percent / Pd(PPh3)4, Na2CO3 / tetrahydrofuran; H2O / 1) rt, 1 h; 2) reflux, 1 h
7: 1.) p-toluenesulfonhydrazide, p-TsOH*H2O, 2.) NaBH3CN / 1) EtOH, reflux, 7 h; 2) EtOH, reflux, 4 h
8: 77 percent / aq. NaOH / ethanol / 0.25 h / 80 °C
View Scheme

: 197963-29-4
2,2-dimethyl-5-phenylpent-4-ynal

: 156897-06-2
licofelone

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: 1.) Et3N, 2.) NaBH(OAc)3 / 1) CH2Cl2, rt, 15 min; 2) CH2Cl2, rt, 12 h 2: 68 percent / pivalic acid / 5 h / 150 °C 3: 77 percent / EtONa / ethanol / 15 h / Ambient temperature 4: 1.) NaH / 1) THF, rt, 1 h; 2) THF, rt, 12 h 5: 92 percent / Pd(PPh3)4, Na2CO3 / tetrahydrofuran; H2O / 1) rt, 1 h; 2) reflux, 1 h 6: 1.) p-toluenesulfonhydrazide, p-TsOH*H2O, 2.) NaBH3CN / 1) EtOH, reflux, 7 h; 2) EtOH, reflux, 4 h 7: 77 percent / aq. NaOH / ethanol / 0.25 h / 80 °C View Scheme
Multi-step reaction with 7 steps 1: 80 percent / NaBH(OAc)3, Et3N / CH2Cl2 / Ambient temperature 2: 68 percent / t-BuCO2H / 150 °C 3: 77 percent / EtONa / ethanol / Ambient temperature 4: 80 percent / NaH / tetrahydrofuran / Ambient temperature 5: 92 percent / Pd(PPh3)4, Na2CO3 / H2O; tetrahydrofuran / Heating 6: 1.) p-toluenesulfonyl hydrazide, p-TsOH, 2.) NaBH3CN / 1.) EtOH, reflux, 2.) EtOH, reflux 7: 77 percent / NaOH / ethanol; H2O / 80 °C View Scheme

Yield

Multi-step reaction with 7 steps
1: 1.) Et3N, 2.) NaBH(OAc)3 / 1) CH2Cl2, rt, 15 min; 2) CH2Cl2, rt, 12 h
2: 68 percent / pivalic acid / 5 h / 150 °C
3: 77 percent / EtONa / ethanol / 15 h / Ambient temperature
4: 1.) NaH / 1) THF, rt, 1 h; 2) THF, rt, 12 h
5: 92 percent / Pd(PPh3)4, Na2CO3 / tetrahydrofuran; H2O / 1) rt, 1 h; 2) reflux, 1 h
6: 1.) p-toluenesulfonhydrazide, p-TsOH*H2O, 2.) NaBH3CN / 1) EtOH, reflux, 7 h; 2) EtOH, reflux, 4 h
7: 77 percent / aq. NaOH / ethanol / 0.25 h / 80 °C
View Scheme

Multi-step reaction with 7 steps
1: 80 percent / NaBH(OAc)3, Et3N / CH2Cl2 / Ambient temperature
2: 68 percent / t-BuCO2H / 150 °C
3: 77 percent / EtONa / ethanol / Ambient temperature
4: 80 percent / NaH / tetrahydrofuran / Ambient temperature
5: 92 percent / Pd(PPh3)4, Na2CO3 / H2O; tetrahydrofuran / Heating
6: 1.) p-toluenesulfonyl hydrazide, p-TsOH, 2.) NaBH3CN / 1.) EtOH, reflux, 2.) EtOH, reflux
7: 77 percent / NaOH / ethanol; H2O / 80 °C
View Scheme

: 197963-31-8
2,2-dimethyl-7-phenyl-2,3,5,6-tetrahydro-1H-pyrrolizin-6-one

: 156897-06-2
licofelone

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 77 percent / EtONa / ethanol / 15 h / Ambient temperature 2: 1.) NaH / 1) THF, rt, 1 h; 2) THF, rt, 12 h 3: 92 percent / Pd(PPh3)4, Na2CO3 / tetrahydrofuran; H2O / 1) rt, 1 h; 2) reflux, 1 h 4: 1.) p-toluenesulfonhydrazide, p-TsOH*H2O, 2.) NaBH3CN / 1) EtOH, reflux, 7 h; 2) EtOH, reflux, 4 h 5: 77 percent / aq. NaOH / ethanol / 0.25 h / 80 °C View Scheme
Multi-step reaction with 5 steps 1: 77 percent / EtONa / ethanol / Ambient temperature 2: 80 percent / NaH / tetrahydrofuran / Ambient temperature 3: 92 percent / Pd(PPh3)4, Na2CO3 / H2O; tetrahydrofuran / Heating 4: 1.) p-toluenesulfonyl hydrazide, p-TsOH, 2.) NaBH3CN / 1.) EtOH, reflux, 2.) EtOH, reflux 5: 77 percent / NaOH / ethanol; H2O / 80 °C View Scheme

: 197963-30-7
methyl N-(2,2-dimethyl-5-phenylpent-4-ynyl)glycinate

: 156897-06-2
licofelone

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 68 percent / pivalic acid / 5 h / 150 °C 2: 77 percent / EtONa / ethanol / 15 h / Ambient temperature 3: 1.) NaH / 1) THF, rt, 1 h; 2) THF, rt, 12 h 4: 92 percent / Pd(PPh3)4, Na2CO3 / tetrahydrofuran; H2O / 1) rt, 1 h; 2) reflux, 1 h 5: 1.) p-toluenesulfonhydrazide, p-TsOH*H2O, 2.) NaBH3CN / 1) EtOH, reflux, 7 h; 2) EtOH, reflux, 4 h 6: 77 percent / aq. NaOH / ethanol / 0.25 h / 80 °C View Scheme
Multi-step reaction with 6 steps 1: 68 percent / t-BuCO2H / 150 °C 2: 77 percent / EtONa / ethanol / Ambient temperature 3: 80 percent / NaH / tetrahydrofuran / Ambient temperature 4: 92 percent / Pd(PPh3)4, Na2CO3 / H2O; tetrahydrofuran / Heating 5: 1.) p-toluenesulfonyl hydrazide, p-TsOH, 2.) NaBH3CN / 1.) EtOH, reflux, 2.) EtOH, reflux 6: 77 percent / NaOH / ethanol; H2O / 80 °C View Scheme

Yield

Multi-step reaction with 6 steps
1: 68 percent / pivalic acid / 5 h / 150 °C
2: 77 percent / EtONa / ethanol / 15 h / Ambient temperature
3: 1.) NaH / 1) THF, rt, 1 h; 2) THF, rt, 12 h
4: 92 percent / Pd(PPh3)4, Na2CO3 / tetrahydrofuran; H2O / 1) rt, 1 h; 2) reflux, 1 h
5: 1.) p-toluenesulfonhydrazide, p-TsOH*H2O, 2.) NaBH3CN / 1) EtOH, reflux, 7 h; 2) EtOH, reflux, 4 h
6: 77 percent / aq. NaOH / ethanol / 0.25 h / 80 °C
View Scheme

Multi-step reaction with 6 steps
1: 68 percent / t-BuCO2H / 150 °C
2: 77 percent / EtONa / ethanol / Ambient temperature
3: 80 percent / NaH / tetrahydrofuran / Ambient temperature
4: 92 percent / Pd(PPh3)4, Na2CO3 / H2O; tetrahydrofuran / Heating
5: 1.) p-toluenesulfonyl hydrazide, p-TsOH, 2.) NaBH3CN / 1.) EtOH, reflux, 2.) EtOH, reflux
6: 77 percent / NaOH / ethanol; H2O / 80 °C
View Scheme

: 197963-32-9
ethyl 2-(2,2-dimethyl-6-hydroxy-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl)-2-oxoacetate

: 156897-06-2
licofelone

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 1.) NaH / 1) THF, rt, 1 h; 2) THF, rt, 12 h 2: 92 percent / Pd(PPh3)4, Na2CO3 / tetrahydrofuran; H2O / 1) rt, 1 h; 2) reflux, 1 h 3: 1.) p-toluenesulfonhydrazide, p-TsOH*H2O, 2.) NaBH3CN / 1) EtOH, reflux, 7 h; 2) EtOH, reflux, 4 h 4: 77 percent / aq. NaOH / ethanol / 0.25 h / 80 °C View Scheme
Multi-step reaction with 4 steps 1: 80 percent / NaH / tetrahydrofuran / Ambient temperature 2: 92 percent / Pd(PPh3)4, Na2CO3 / H2O; tetrahydrofuran / Heating 3: 1.) p-toluenesulfonyl hydrazide, p-TsOH, 2.) NaBH3CN / 1.) EtOH, reflux, 2.) EtOH, reflux 4: 77 percent / NaOH / ethanol; H2O / 80 °C View Scheme

Raw Materials

116673-95-1

100-44-7

79-37-8

126-30-7

133111-56-5

3355-31-5

1003-85-6

536-38-9

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Specification

The Licofelone is an organic compound with the formula C₂₃H₂₂ClNO₂. The systematic name of this chemical is [6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl]acetic acid. With the CAS registry number 156897-06-2, it is also named as (2,2-dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine-5-yl)acetic acid. The product's categories are Intermediates & Fine Chemicals; Pharmaceuticals. Besides, it is a dual COX/LOX inhibitor being considered as a treatment for osteoarthritis. Licofelone is both an analgesic and an anti-inflammatory. Inhibition of 5-LOX may reduce the gastrointestinal toxicity associated with other non-steroidal anti-inflammatory drugs, which only inhibit COX (cyclooxygenase).

Physical properties about Licofelone are: (1)ACD/LogP: 6.73; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 5.66; (4)ACD/LogD (pH 7.4): 3.86; (5)ACD/BCF (pH 5.5): 6567.38; (6)ACD/BCF (pH 7.4): 103.76; (7)ACD/KOC (pH 5.5): 9340.49; (8)ACD/KOC (pH 7.4): 147.58; (9)#H bond acceptors: 3; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 31.23 Å²; (13)Index of Refraction: 1.626; (14)Molar Refractivity: 108.77 cm³; (15)Molar Volume: 306.9 cm³; (16)Polarizability: 43.12×10^-24cm³; (17)Surface Tension: 45.5 dyne/cm; (18)Density: 1.23 g/cm³; (19)Flash Point: 280.2 °C; (20)Enthalpy of Vaporization: 86.01 kJ/mol; (21)Boiling Point: 539.7 °C at 760 mmHg; (22)Vapour Pressure: 1.76E-12 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: Clc4ccc(c1c(n3c(c1c2ccccc2)CC(C)(C3)C)CC(=O)O)cc4
(2)InChI: InChI=1/C23H22ClNO2/c1-23(2)13-19-22(15-6-4-3-5-7-15)21(16-8-10-17(24)11-9-16)18(12-20(26)27)25(19)14-23/h3-11H,12-14H2,1-2H3,(H,26,27)
(3)InChIKey: UAWXGRJVZSAUSZ-UHFFFAOYAP
(4)Std. InChI: InChI=1S/C23H22ClNO2/c1-23(2)13-19-22(15-6-4-3-5-7-15)21(16-8-10-17(24)11-9-16)18(12-20(26)27)25(19)14-23/h3-11H,12-14H2,1-2H3,(H,26,27)
(5)Std. InChIKey: UAWXGRJVZSAUSZ-UHFFFAOYSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD	oral	> 300mg/kg (300mg/kg)		Arzneimittel-Forschung. Drug Research. Vol. 45, Pg. 159, 1995.