1-(3-Ethoxy-4-methoxy-phenyl)-2-methanesulfonyl-ethylamine (Apremilast Intermediate)

CAS Number: 253168-94-4

Molecular Formula: C12H19NO4S

Selective Phosphodiesterase 4 (PDE4) InhibitorClinical Indications: Psoriatic Arthritis, Plaque Psoriasis, Behçet's DiseaseBulk aminosulfone manufacturingOtezla intermediate supplyWholesale pharmaceutical building blockGMP Grade apremilast building block

About 1-(3-Ethoxy-4-methoxy-phenyl)-2-methanesulfonyl-ethylamine (Apremilast Intermediate)

Apremilast Intermediate (CAS 253168-94-4), chemically identified as 1-(3-Ethoxy-4-methoxy-phenyl)-2-methanesulfonyl-ethylamine, a pivotal aminosulfone building block. In pharmaceutical landscape, this intermediate serves as the essential chiral precursor for the synthesis of Apremilast (Otezla), a blockbuster oral ther...

1-(3-Ethoxy-4-methoxy-phenyl)-2-methanesulfonyl-ethylamine (Apremilast Intermediate) Specifications

CAS Number

253168-94-4

Molecular Formula

C12H19NO4S

Molecular Weight

273.35

IUPAC Name

1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethanamine

Canonical SMILES

CCOC1=C(C=CC(=C1)C(CS(=O)(=O)C)N)OC

InChI Key

BXUJVINGXQGNFD-UHFFFAOYSA-N

InChI

1S/C12H19NO4S/c1-4-17-12-7-9(5-6-11(12)16-2)10(13)8-18(3,14)15/h5-7,10H,4,8,13H2,1-3H3

MDL Number

MFCD27665207

CAS Number

253168-94-4

Molecular Formula

C12H19NO4S

Molecular Weight

273.35

IUPAC Name

1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethanamine

Canonical SMILES

CCOC1=C(C=CC(=C1)C(CS(=O)(=O)C)N)OC

InChI Key

BXUJVINGXQGNFD-UHFFFAOYSA-N

InChI

1S/C12H19NO4S/c1-4-17-12-7-9(5-6-11(12)16-2)10(13)8-18(3,14)15/h5-7,10H,4,8,13H2,1-3H3

MDL Number

MFCD27665207

Molecular Weight

273.35

Boiling Point (Predicted)

469.577+45.00 °C Press: 760.00 Torr

Density (Predicted)

1.195+0.06 g/cm Temp: 25°C; Press: 760 Torr

pKa (Predicted)

6.835+0.10 Most Basic Temp: 25 °C

Hazard Classes and Categories

Acute Tox. 4 (66.7%), Acute Tox. 4 (66.7%), Skin Irrit. 2 (33.3%), Eye Irrit. 2 (33.3%), Acute Tox. 4 (66.7%)

Precautionary Statement Codes

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P321, P330, P332+P317, P337+P317, P362+P364, and P501

Primary Precursor

Late-stage condensation with 3-acetamidophthalic anhydride to form Apremilast

Enantioselective Synthesis

Catalytic asymmetric hydrogenation routes to bypass expensive chiral resolution steps

Apremilast EP Impurity H

In regulatory environments-Tracked as "process-related impurity" under ICH Q3A/Q3B guidelines

Stability Studies

Validate HPLC and LC-MS methods for drug substance purity testing by QC laboratories

Inhibitor Scaffolds

Chemical "node" for developing next-generation PDE4 inhibitors for respiratory conditions (Asthma/COPD) and neuroinflammatory research

(MOA)

As a PDE4 inhibitor, it works by increasing intracellular levels of cyclic adenosine monophosphate (cAMP). This e levation indirectly modulates the production of numerous inflammatory mediators Down-regulates: Pro-inflammatory cytokines like TNF-a, IL-23, and Interferon-gamma (IFN-Y) Up-regulates: Anti-inflammatory cytokines like IL-10