NBI-74330

Base Information

• Chemical Name: NBI-74330
• CAS No.: 855527-92-3
• Molecular Formula: C₃₂H₂₇F₄N₅O₃
• Molecular Weight: 605.592
• Mol file: 855527-92-3.mol

Synonyms:NBI-74330;N-[(1R)-1-[3-(4-Ethoxyphenyl)-3,4-dihydro-4-oxopyrido[2,3-d]pyrimidin-2-yl]ethyl]-4-fluoro-N-(3-pyridinylmethyl)-3-(trifluoromethyl)benzeneacetamide;(R)-N-(1-(3-(4-Ethoxyphenyl)-4-oxo-3,4-dihydropyrido[2,3-d]pyrimidin-2-yl)ethyl)-2-(4-fluoro-3-(trifluoromethyl)phenyl)-N-(pyridin-3-ylmethyl)acetamide;Benzeneacetamide, N-[(1R)-1-[3-(4-ethoxyphenyl)-3,4-dihydro-4-oxopyrido[2,3-d]pyrimidin-2-yl]ethyl]-4-fluoro-N-(3-pyridinylmethyl)-3-(trifluoromethyl)-

Chemical Property of NBI-74330

Chemical Property:

• Boiling Point: 752.5±70.0 °C(Predicted)
• PKA: 4?+-.0.11(Predicted)
• PSA: 90.21000
• Density: 1.32±0.1 g/cm3(Predicted)
• LogP: 6.06480

Purity/Quality:

97% ^*data from raw suppliers

NBI-74330 98+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: NBI 74330 is a chemokine (C-X-C motif) receptor 3 (CXCR3) antagonist (Ki = 3.6 nM in a radioligand binding assay). It inhibits calcium mobilization induced by chemokine (C-X-C motif) ligand 10 (CXCL10) or CXCL11 in RBL cells expressing human CXCR3 (IC50 = 7 nM for both). NBI 74330 inhibits CXCL11-induced chemotaxis of CXCR3-expressing H9 cells and PHA and IL-2 differentiated T cells (IC50s = 3.9 and 6.6 nM, respectively). In vivo, NBI 74330 (100 mg/kg) reduces peritoneal lymphocyte migration in a mouse model of peritonitis. It reduces the size and number of aortic arch atherosclerotic lesions in Ldlr-/- mice. NBI 74330 reduces spinal cord microglial activation and levels of CXCL4, CXCL9, and CXCL10 and decreases thermal and mechanical hyperalgesia in a rat model of chronic constriction injury-induced neuropathic pain.
• Uses: N-[(1R)-1-[3-(4-Ethoxyphenyl)-3,4-dihydro-4-oxopyrido[2,3-d]pyrimidin-2-yl]ethyl]-4-fluoro-N-(3-pyridinylmethyl)-3-(trifluoromethyl)benzeneacetamide is a CXCR3 antagonist.

Technology Process of NBI-74330

There total 10 articles about NBI-74330 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 19.0%

rac-3-(4-ethoxy-phenyl)-2-{1-[(pyridin-3-ylmethyl)-amino]-ethyl}-3H-pyrido[2,3-d]pyrimidin-4-one (947536-02-9) + (4-fluoro-3-trifluoromethyl-phenyl)-acetic acid (220227-47-4) → (+/-)-NBI-74330 (855527-92-3,473722-68-8)

Guidance literature:

(4-fluoro-3-trifluoromethyl-phenyl)-acetic acid; With 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane;

rac-3-(4-ethoxy-phenyl)-2-{1-[(pyridin-3-ylmethyl)-amino]-ethyl}-3H-pyrido[2,3-d]pyrimidin-4-one; In dichloromethane; Further stages.;

DOI:10.1002/ardp.200700037

Reference yield:

(4-fluoro-3-trifluoromethyl-phenyl)-acetic acid (220227-47-4) + C23H23N5O2 (473720-92-2) → NBI 74330 (855527-92-3,473722-68-8)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

DOI:10.1016/j.bmcl.2009.07.032

Reference yield:

rac-2-(1-amino-ethyl)-3-(4-ethoxy-phenyl)-3H-pyrido[2,3-d]pyrimidin-4-one (947536-13-2) + (4-fluoro-3-trifluoromethyl-phenyl)-acetic acid (220227-47-4) → (+/-)-NBI-74330 (855527-92-3,473722-68-8)

Guidance literature:

With 2-(1H-9-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluroniumhexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 45 ℃; for 20h;

DOI:10.1002/cmdc.201200184

upstream raw materials:

(4-fluoro-3-trifluoromethyl-phenyl)-acetic acid

C₂₃H₂₃N₅O₂

rac-3-(4-ethoxy-phenyl)-2-{1-[(pyridin-3-ylmethyl)-amino]-ethyl}-3H-pyrido[2,3-d]pyrimidin-4-one

(R)-[1-(4-oxo-4H-pyrido[2,3-d][1,3]oxazin-2-yl)-ethyl]-carbamic acid tert-butyl ester

Downstream raw materials:

C₃₂H₂₇F₄N₅O₄