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168273-06-1

Basic Information
CAS No.: 168273-06-1
Name: Rimonabant
Article Data: 35
Molecular Structure:
Molecular Structure of 168273-06-1 (Rimonabant)
Formula: C22H21Cl3N4O
Molecular Weight: 463.794
Synonyms: 1-(2,4-Dichlorophenyl)-5-(4-chlorophenyl)-4-methyl-N-(piperidin-1-yl)-1H-pyrazole-3-carboxamide;5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylicacid N-(piperidin-1-yl)amide;A 281;Acomplia;N-Piperidino-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazole-3-carboxamide;SR 141716;
Density: 1.41 g/cm3
Melting Point: 230-240oC
Boiling Point: 627.6oC at 760 mmHg
Flash Point: 333.3oC
Appearance: White or almost white crystalline powder
PSA: 50.16000
LogP: 6.26740
Synthetic route
158681-13-1

rimonabant hydrochloride

168273-06-1

rimonabant

Conditions
ConditionsYield
With methanol; potassium hydroxide; water at 0 - 5℃; for 1h;93%
With sodium hydroxide In methanol; water pH=8.5;
With sodium hydroxide In methanol; water at 28 - 30℃; for 0.666667h; pH=11;
2213-43-6

1-Aminopiperidine

158941-22-1

ethyl 1-(2,4-dichlorophenyl)-4-methyl-5-(4-chlorophenyl)-1H-pyrazole-3-carboxylate

168273-06-1

rimonabant

Conditions
ConditionsYield
With trimethylaluminum In tetrahydrofuran; toluene at 125℃; for 0.0333333h;88%
magnesium chloride In acetonitrile for 2h; Product distribution / selectivity; Heating / reflux;83%
magnesium bromide In tetrahydrofuran for 2h; Product distribution / selectivity; Heating / reflux;81%
168272-78-4

5-(4-Chloro-phenyl)-1-(2,4-dichloro-phenyl)-4-methyl-1H-pyrazole-3-carboxylic acid methyl ester

2213-43-6

1-Aminopiperidine

168273-06-1

rimonabant

Conditions
ConditionsYield
magnesium chloride In tetrahydrofuran for 2h; Product distribution / selectivity; Heating / reflux;82%
magnesium chloride In acetonitrile for 2h; Product distribution / selectivity; Heating / reflux;80%
magnesium bromide In tetrahydrofuran for 2h; Product distribution / selectivity; Heating / reflux;79%
2213-43-6

1-Aminopiperidine

168273-05-0

5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carbonyl chloride

168273-06-1

rimonabant

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 12h;79%
With triethylamine In dichloromethane at 20℃; for 1.5h; Substitution;66%
With triethylamine Yield given;
1030616-35-3

phenyl 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylate

2213-43-6

1-Aminopiperidine

168273-06-1

rimonabant

Conditions
ConditionsYield
magnesium chloride In acetonitrile for 2h; Product distribution / selectivity; Heating / reflux;77%
magnesium chloride In acetonitrile at 80℃; for 2 - 4h; Product distribution / selectivity;
63234-70-8

N-aminopiperidine hydrochloride

158941-22-1

ethyl 1-(2,4-dichlorophenyl)-4-methyl-5-(4-chlorophenyl)-1H-pyrazole-3-carboxylate

168273-06-1

rimonabant

Conditions
ConditionsYield
With triethylamine; magnesium chloride In acetonitrile for 4h; Product distribution / selectivity; Heating / reflux;77%
Stage #1: N-aminopiperidine hydrochloride With potassium tert-butylate In acetonitrile at 20℃; for 0.5h;
Stage #2: ethyl 1-(2,4-dichlorophenyl)-4-methyl-5-(4-chlorophenyl)-1H-pyrazole-3-carboxylate; magnesium chloride In acetonitrile for 4h; Product distribution / selectivity; Heating / reflux;
61%
1030616-37-5

N-aminopiperidine hydrogen sulphate

158941-22-1

ethyl 1-(2,4-dichlorophenyl)-4-methyl-5-(4-chlorophenyl)-1H-pyrazole-3-carboxylate

168273-06-1

rimonabant

Conditions
ConditionsYield
With triethylamine; magnesium chloride In acetonitrile for 4h; Product distribution / selectivity; Heating / reflux;77%
2213-43-6

1-Aminopiperidine

162758-35-2

rimonabant acid

168273-06-1

rimonabant

Conditions
ConditionsYield
Stage #1: rimonabant acid With benzotriazol-1-ol In dichloromethane for 0.166667h;
Stage #2: With dicyclohexyl-carbodiimide In dichloromethane at 25℃;
Stage #3: 1-Aminopiperidine Further stages;
72%
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 72h;68%
Stage #1: rimonabant acid With thionyl chloride In methyl cyclohexane at 83℃; for 3h; Heating / reflux;
Stage #2: With triethylamine In tetrahydrofuran; methyl cyclohexane at 12 - 20℃; for 0.25h;
Stage #3: 1-Aminopiperidine With triethylamine In tetrahydrofuran; methyl cyclohexane at 12 - 20℃; Product distribution / selectivity;
With 1,1'-carbonyldiimidazole In tetrahydrofuran at 65 - 70℃; for 2.33333h; Product distribution / selectivity;
With boric acid In toluene at 29 - 112℃; for 12.83h; Product distribution / selectivity;
1040405-33-1

5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid(2,6-benzotriazolyl-piperidin-1-yl)amide

168273-06-1

rimonabant

Conditions
ConditionsYield
With sodium tetrahydroborate In tetrahydrofuran at 20℃;46%
2213-43-6

1-Aminopiperidine

168273-05-0

5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carbonyl chloride

A

168273-06-1

rimonabant

B

N-(piperidin-1-yl)-3-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-5-carboxamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 2h;A 11.5 g
B 645 mg
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158681-13-1
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Specification

The 1H-Pyrazole-3-carboxamide,5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-1-piperidinyl- is an organic compound with the formula C22H21Cl3N4O. The IUPAC name of this chemical is 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-piperidin-1-ylpyrazole-3-carboxamide. With the CAS registry number 168273-06-1, it is also named as Rimonabant. The product's category is Weight Loss.

Physical properties about 1H-Pyrazole-3-carboxamide,5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-1-piperidinyl- are: (1)ACD/LogP: 6.14; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 6.14; (4)ACD/LogD (pH 7.4): 6.14; (5)ACD/BCF (pH 5.5): 27061.6; (6)ACD/BCF (pH 7.4): 27198.54; (7)ACD/KOC (pH 5.5): 51715.72; (8)ACD/KOC (pH 7.4): 51977.41; (9)#H bond acceptors: 5; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 41.37 Å2; (13)Index of Refraction: 1.668; (14)Molar Refractivity: 122.23 cm3; (15)Molar Volume: 327.8 cm3; (16)Polarizability: 48.45×10-24cm3; (17)Surface Tension: 51.2 dyne/cm; (18)Density: 1.41 g/cm3.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(NN1CCCCC1)c4nn(c2ccc(Cl)cc2Cl)c(c3ccc(Cl)cc3)c4C
(2)InChI: InChI=1/C22H21Cl3N4O/c1-14-20(22(30)27-28-11-3-2-4-12-28)26-29(19-10-9-17(24)13-18(19)25)21(14)15-5-7-16(23)8-6-15/h5-10,13H,2-4,11-12H2,1H3,(H,27,30)
(3)InChIKey: JZCPYUJPEARBJL-UHFFFAOYAO
(4)Std. InChI: InChI=1S/C22H21Cl3N4O/c1-14-20(22(30)27-28-11-3-2-4-12-28)26-29(19-10-9-17(24)13-18(19)25)21(14)15-5-7-16(23)8-6-15/h5-10,13H,2-4,11-12H2,1H3,(H,27,30)
(5)Std. InChIKey: JZCPYUJPEARBJL-UHFFFAOYSA-N