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| CAS No.: | 162401-32-3 |
|---|---|
| Name: | Roflumilast |
| Molecular Structure: | |
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| Formula: | C17H14Cl2F2N2O3 |
| Molecular Weight: | 403.213 |
| Synonyms: | B 9302-107;BY 217;BYK 20869;Daxas;3-(Cyclopropylmethoxy)-N-(3,5-dichloropyridin-4-yl)-4-(difluoromethoxy)benzamide; |
| EINECS: | 685-382-2 |
| Density: | 1.471 g/cm3 |
| Melting Point: | 158 °C |
| Boiling Point: | 430.6 °C at 760 mmHg |
| Flash Point: | 214.2 °C |
| Appearance: | Crystalline solid |
| Hazard Symbols: | Xi |
| Risk Codes: | 36/37/38 |
| Safety: | 26 |
| PSA: | 60.45000 |
| LogP: | 5.10390 |
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- 211914-50-0N-[[2-[[[4-(Aminoiminomethyl)phenyl]amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl]-N-(2-pyridinyl)-beta-alanine ethyl ester hydrochloride
- 162401-62-9
3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzoic acid
- 22889-78-7
3,5-dichloro-4-aminopyridine
- 162401-32-3
roflumilast
| Conditions | Yield |
|---|---|
| Stage #1: 3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzoic acid With pyridine; 2,4,6-trinitrochlorobenzene In 1,4-dioxane at 20 - 35℃; for 3h; Industrial scale; Stage #2: 3,5-dichloro-4-aminopyridine In 1,4-dioxane for 2h; Reagent/catalyst; Solvent; Temperature; Industrial scale; | 95% |
| Stage #1: 3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzoic acid With 4-methyl-morpholine; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine In dichloromethane at 0 - 20℃; for 3h; Stage #2: 3,5-dichloro-4-aminopyridine In dichloromethane for 2h; Concentration; | 91% |
| Stage #1: 3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzoic acid With pivaloyl chloride; sodium carbonate In tetrahydrofuran at 25℃; for 2h; Stage #2: 3,5-dichloro-4-aminopyridine In tetrahydrofuran at 50℃; for 4h; Temperature; Solvent; Reagent/catalyst; | 64% |
| Stage #1: 3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzoic acid With thionyl chloride In toluene Heating / reflux; Stage #2: 3,5-dichloro-4-aminopyridine With sodium hydride In tetrahydrofuran for 1h; Cooling; | 58.6% |
- 22889-78-7
3,5-dichloro-4-aminopyridine
- 162401-69-6
3-(difluoromethoxy)-4-(cyclopropylmethoxy)-benzoic acid
- 162401-32-3
roflumilast
| Conditions | Yield |
|---|---|
| Stage #1: 3-(difluoromethoxy)-4-(cyclopropylmethoxy)-benzoic acid With thionyl chloride In toluene for 2h; Reflux; Stage #2: 3,5-dichloro-4-aminopyridine With sodium hydride In tetrahydrofuran at 15 - 20℃; | 95% |
- 162401-62-9
3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzoic acid
- 162401-32-3
roflumilast
| Conditions | Yield |
|---|---|
| Large scale; | 93% |
| Multi-step reaction with 2 steps 1.1: dimethyl sulfoxide / 3 h / 20 °C 2.1: cesium fluoride / dimethyl sulfoxide / 3 h / 90 °C 2.2: 6.5 h / 90 - 95 °C View Scheme |
- 1454574-39-0
3,5-dichloro-N-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)benzylidene)pyridin-4-amine
- 162401-32-3
roflumilast
| Conditions | Yield |
|---|---|
| With sodium chlorite; 2-methyl-but-2-ene; acetic acid In water; acetonitrile at 20 - 30℃; for 3h; Cooling with ice; | 92.4% |
| With sodium chlorite; 2-methyl-but-2-ene; acetic acid In water; acetonitrile at 20 - 30℃; for 2h; Reagent/catalyst; Cooling with ice; | 82% |
| With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene In tetrahydrofuran; water | 57% |
- 22889-78-7
3,5-dichloro-4-aminopyridine
- 1590361-85-5
(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)(1H-imidazol-1-yl)methanone
- 162401-32-3
roflumilast
| Conditions | Yield |
|---|---|
| Stage #1: 3,5-dichloro-4-aminopyridine With cesium fluoride In dimethyl sulfoxide at 90℃; for 3h; Stage #2: (3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)(1H-imidazol-1-yl)methanone In dimethyl sulfoxide at 90 - 95℃; for 6.5h; Reagent/catalyst; | 88% |
| Conditions | Yield |
|---|---|
| With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 2h; Temperature; | 82.3% |
- 22889-78-7
3,5-dichloro-4-aminopyridine
- 1601300-21-3
(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)(1H-1,2,4-triazol-1-yl)methanone
- 162401-32-3
roflumilast
| Conditions | Yield |
|---|---|
| Stage #1: 3,5-dichloro-4-aminopyridine With cesium fluoride In dimethyl sulfoxide at 90℃; for 3h; Stage #2: (3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)(1H-1,2,4-triazol-1-yl)methanone In dimethyl sulfoxide at 90 - 95℃; for 3h; | 79% |
- 672883-68-0
3-(cyclopropylmethoxy)-4-(difluoromethoxy)benzoyl chloride
- 162401-32-3
roflumilast
| Conditions | Yield |
|---|---|
| In DMF (N,N-dimethyl-formamide) at 15 - 40℃; | |
| In 1-methyl-pyrrolidin-2-one at 15 - 40℃; | |
| In DMF (N,N-dimethyl-formamide) at 15 - 40℃; | |
| In DMF (N,N-dimethyl-formamide) at 15 - 40℃; | |
| In tetrahydrofuran at 0 - 10℃; for 2.5h; |
- 22889-78-7
3,5-dichloro-4-aminopyridine
- 672883-68-0
3-(cyclopropylmethoxy)-4-(difluoromethoxy)benzoyl chloride
- 162401-32-3
roflumilast
| Conditions | Yield |
|---|---|
| With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; | |
| Stage #1: 3,5-dichloro-4-aminopyridine With sodium hydroxide In toluene for 2h; Stage #2: 3-(cyclopropylmethoxy)-4-(difluoromethoxy)benzoyl chloride In toluene for 6h; Concentration; Temperature; Time; Reflux; | 89.2 %Chromat. |
| Stage #1: 3,5-dichloro-4-aminopyridine With sodium hydride In tetrahydrofuran for 0.5h; Stage #2: 3-(cyclopropylmethoxy)-4-(difluoromethoxy)benzoyl chloride In tetrahydrofuran at 20 - 30℃; for 1h; |
- 58123-77-6
3-hydroxy-4-iodobenzoic acid
- 162401-32-3
roflumilast
| Conditions | Yield |
|---|---|
| Multi-step reaction with 7 steps 1: thionyl chloride / 3 h / 50 °C 2: potassium carbonate / N,N-dimethyl-formamide / 2 h / 80 °C / Large scale 3: potassium hydroxide; copper(l) iodide; 8-quinolinol / dimethyl sulfoxide / 30 h / 100 °C / Inert atmosphere; Large scale 4: thionyl chloride / 3 h / 50 °C 5: potassium carbonate / N,N-dimethyl-formamide / 1.25 h / 95 °C 6: sodium hydroxide / methanol / 3 h / 50 °C 7: Large scale View Scheme | |
| Multi-step reaction with 7 steps 1: thionyl chloride / 3 h / 50 °C 2: potassium carbonate / N,N-dimethyl-formamide / 2 h / 80 °C / Large scale 3: potassium hydroxide; copper(l) iodide; 8-quinolinol / dimethyl sulfoxide / 30 h / 100 °C / Inert atmosphere; Large scale 4: thionyl chloride / 3 h / 50 °C 5: N,N-dimethyl-formamide / Heating 6: sodium hydroxide / methanol / 3 h / 50 °C 7: Large scale View Scheme |
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Specification
The IUPAC name of Roflumilast is 3-(cyclopropylmethoxy)-N-(3,5-dichloropyridin-4-yl)-4-(difluoromethoxy)benzamide. With the CAS registry number 162401-32-3, it is also named as Benzamide, 3-(cyclopropylmethoxy)-N-(3,5-dichloro-4-pyridinyl)-4-(difluoromethoxy)-. The product's categories are All Inhibitors; Inhibitors; Intermediates & Fine Chemicals; Pharmaceuticals. It is crystalline solid which is a drug which acts as a selective, long-acting inhibitor of the enzyme PDE-4.
The other characteristics of this product can be summarized as: (1)ACD/LogP4.24: ; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 4.24; (4)ACD/LogD (pH 7.4): 4.24; (5)ACD/BCF (pH 5.5): 975.07; (6)ACD/BCF (pH 7.4): 983.7; (7)ACD/KOC (pH 5.5): 4786.84; (8)ACD/KOC (pH 7.4): 4829.22; (9)#H bond acceptors: 5; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 7; (12)Index of Refraction: 1.599; (13)Molar Refractivity: 93.97 cm3; (14)Molar Volume: 274.8 cm3; (15)Polarizability: 37.25×10-24 cm3; (16)Surface Tension: 52.8 dyne/cm; (17)Enthalpy of Vaporization: 73.36 kJ/mol; (18)Vapour Pressure: 4.86E-09 mmHg at 25°C; (19)Rotatable Bond Count: 7; (20)Tautomer Count: 3; (21)Exact Mass: 402.034954; (22)MonoIsotopic Mass: 402.034954; (23)Topological Polar Surface Area: 60.4; (24)Heavy Atom Count: 26; (25)Complexity: 475.
Preparation of Roflumilast: It can be obtained by the following method:
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Uses of Roflumilast: It has antiinflammatory effects and is under development as an orally administered drug for the treatment of inflammatory conditions of the lungs such as asthma, and chronic obstructive pulmonary disease (COPD).
People can use the following data to convert to the molecule structure.
1. SMILES:Clc3c(N(OCC1CC1)C(=O)c2ccc(OC(F)F)cc2)c(Cl)cnc3
2. InChI:InChI=1/C17H14Cl2F2N2O3/c18-13-7-22-8-14(19)15(13)23(25-9-10-1-2-10)16(24)11-3-5-12(6-4-11)26-17(20)21/h3-8,10,17H,1-2,9H2
3. InChIKey:IWONQDOIPBAXGV-UHFFFAOYAH