CAS No.608141-41-9,ApreMilast Suppliers

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Basic Information

Molecular Structure:
CAS No.:	608141-41-9
Name:	ApreMilast
Article Data:	55

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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
at 135 - 139℃; Large scale;	98.2%
at 70℃; for 3h; Inert atmosphere; enantioselective reaction;	94%
at 70℃; for 3h;	97 %Chromat.

Raw Materials

603-11-2

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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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