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608141-41-9

Basic Information
CAS No.: 608141-41-9
Name: ApreMilast
Article Data: 55
Molecular Structure:
Molecular Structure of 608141-41-9 (ApreMilast)
Formula: C22H24N2O7S
Molecular Weight: 460.508
Synonyms: CC 10004;(S)-N-(2-(1-(3-Ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl)-1,3-dioxoisoindolin-4-yl)acetamide;(S)-2-[1-(3-Ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-acetylaminoisoindoline-1,3-dione;
EINECS: 807-237-6
Density: 1.382 g/cm3
Boiling Point: 741.342 °C at 760 mmHg
Flash Point: 402.149 °C
PSA: 127.46000
LogP: 3.52590
Synthetic route
635705-72-5

4-amino-2-[(1S)-1-(3-ethoxy 4-methoxyphenyl)-2-methanesulfonylethyl]-2,3-dihydro-1H-isoindole-1,3-dione

108-24-7

acetic anhydride

608141-41-9

Apremilast

Conditions
ConditionsYield
at 135 - 139℃; Large scale;98.2%
at 70℃; for 3h; Inert atmosphere; enantioselective reaction;94%
6296-53-3

3-acetylaminophthalic anhydride

608141-42-0

(S)-2-[1 (3-ethoxy-4-methoxyphenyl)]-1-methanesulfonyl-2-ethylamine

608141-41-9

Apremilast

Conditions
ConditionsYield
With acetic acid for 1h; Reflux; Large scale;97%
With acetic acid In acetonitrile at 40℃; for 6h; Reflux;94%
With acetic acid for 3h; Time; Reflux;92%
6296-53-3

3-acetylaminophthalic anhydride

608141-43-1

(S)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethanamine-(S)-2-acetamido-4-methylpentanoate

608141-41-9

Apremilast

Conditions
ConditionsYield
With triethylamine In ethyl acetate at 75 - 80℃; for 18h; Reagent/catalyst; Solvent;95.1%
With sodium acetate; acetic acid at 80℃; for 5h; Reagent/catalyst; Temperature;91.3%
Stage #1: (S)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethanamine-(S)-2-acetamido-4-methylpentanoate With sodium hydroxide In dichloromethane at 0 - 5℃; for 2h;
Stage #2: 3-acetylaminophthalic anhydride With perchloric acid; acetic acid In dichloromethane at 45℃; for 3.33333h; Reflux;
89.2%
6296-53-3

3-acetylaminophthalic anhydride

(1S)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylthio)ethan-1-amine

608141-41-9

Apremilast

Conditions
ConditionsYield
Stage #1: 3-acetylaminophthalic anhydride; (1S)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylthio)ethan-1-amine With acetic acid In acetonitrile for 12h; Reflux;
Stage #2: With sodium tungstate (VI) dihydrate; dihydrogen peroxide In acetonitrile at 20℃; for 7h; Cooling;
94%
Multi-step reaction with 2 steps
1.1: acetic acid / acetonitrile / 12 h / Reflux
2.1: acetic acid / acetonitrile / 20 °C
2.2: 7 h / 20 °C
View Scheme

N-[2-[(1S)-1-(3-ethoxy-4-methoxyphenyl)(methylthio)ethyl]-2,3-dihydro-1,3-dioxo-1H-isoindol-4-yl]acetamide

608141-41-9

Apremilast

Conditions
ConditionsYield
Stage #1: N-[2-[(1S)-1-(3-ethoxy-4-methoxyphenyl)(methylthio)ethyl]-2,3-dihydro-1,3-dioxo-1H-isoindol-4-yl]acetamide With acetic acid In acetonitrile at 20℃;
Stage #2: With sodium tungstate (VI) dihydrate; dihydrogen peroxide In acetonitrile at 20℃; for 7h;
91%
608141-43-1

(S)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethanamine-(S)-2-acetamido-4-methylpentanoate

15371-06-9

3-acetylaminophthalic acid

608141-41-9

Apremilast

Conditions
ConditionsYield
With acetic acid at 100 - 120℃; for 2h; Reagent/catalyst;86.7%
With acetic acid at 110 - 115℃; for 1h;3.4 g
6296-53-3

3-acetylaminophthalic anhydride

C12H19NO4S*C10H10ClNO5

608141-41-9

Apremilast

Conditions
ConditionsYield
With acetic acid for 24h; Time; Reflux;85%
6296-53-3

3-acetylaminophthalic anhydride

(R,R)-O,O’-di-p-toluoyl-tartrate

608141-41-9

Apremilast

Conditions
ConditionsYield
With acetic acid for 24h; Reflux;83%
635705-72-5

4-amino-2-[(1S)-1-(3-ethoxy 4-methoxyphenyl)-2-methanesulfonylethyl]-2,3-dihydro-1H-isoindole-1,3-dione

75-36-5

acetyl chloride

608141-41-9

Apremilast

Conditions
ConditionsYield
With iodine In dichloromethane at 25 - 30℃;81%
With potassium carbonate In ethyl acetate at 25 - 30℃; for 3h; Solvent; Temperature; Concentration; Reflux;9 g
635705-72-5

4-amino-2-[(1S)-1-(3-ethoxy 4-methoxyphenyl)-2-methanesulfonylethyl]-2,3-dihydro-1H-isoindole-1,3-dione

108-24-7

acetic anhydride

608141-41-9

Apremilast

Conditions
ConditionsYield
at 135 - 139℃; Large scale;98.2%
at 70℃; for 3h; Inert atmosphere; enantioselective reaction;94%
at 70℃; for 3h;97 %Chromat.
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    Specification Product Name:Apremilast Product number:BJM-041 CAS:608141-41-9 Molecular formula:C22H24N2O7S Molecular weight:460.5 Content:99.0%min Alisa: Apremilast (CC-10004) ; Otezla MW: 460.50 Density: 1.382 g/cm3 Boiling point: 741.342 °C

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Specification

The Apremilast, with the CAS registry number 608141-41-9, is also known as (S)-2-[1-(3-Ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-acetylaminoisoindoline-1,3-dione. This chemical's molecular formula is C22H24N2O7S and molecular weight is 460.50. What's more, its systematic name is N-{2-[(1S)-1-(3-Ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl]-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl}acetamide. Its classification code is Treatment of chronic inflammatory conditions including psoriasis, arthritis, asthma and cutaneous lupus erythematosus (CLE). This chemical is an orally available small molecule inhibitor of PDE4 being developed by Celgene for ankylosing spondylitis, psoriasis, and psoriatic arthritis

Physical properties of Apremilast are: (1)ACD/LogP: 1.754; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.75; (4)ACD/LogD (pH 7.4): 1.75; (5)ACD/BCF (pH 5.5): 12.68; (6)ACD/BCF (pH 7.4): 12.68; (7)ACD/KOC (pH 5.5): 214.35; (8)ACD/KOC (pH 7.4): 214.35; (9)#H bond acceptors: 9; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 8; (12)Polar Surface Area: 127.46 Å2; (13)Index of Refraction: 1.612; (14)Molar Refractivity: 115.86 cm3; (15)Molar Volume: 333.272 cm3; (16)Polarizability: 45.931×10-24cm3; (17)Surface Tension: 60.6 dyne/cm; (18)Density: 1.382 g/cm3; (19)Flash Point: 402.149 °C; (20)Enthalpy of Vaporization: 108.117 kJ/mol; (21)Boiling Point: 741.342 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=S(=O)(C)C[C@H](c1ccc(OC)c(OCC)c1)N3C(=O)c2cccc(c2C3=O)NC(=O)C
(2)Std. InChI: InChI=1S/C22H24N2O7S/c1-5-31-19-11-14(9-10-18(19)30-3)17(12-32(4,28)29)24-21(26)15-7-6-8-16(23-13(2)25)20(15)22(24)27/h6-11,17H,5,12H2,1-4H3,(H,23,25)/t17-/m1/s1
(3)Std. InChIKey: IMOZEMNVLZVGJZ-QGZVFWFLSA-N

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