Ubrogepant

Base Information

• Chemical Name: Ubrogepant
• CAS No.: 1374248-77-7
• Molecular Formula: C₂₉H₂₆F₃N₅O₃
• Molecular Weight: 549.552
• Mol file: 1374248-77-7.mol

Synonyms:Ubrogepant

Chemical Property of Ubrogepant

Chemical Property:

• Boiling Point: 729.4±60.0 °C(Predicted)
• PKA: 11.08±0.20(Predicted)
• PSA: 104.29000
• Density: 1.45±0.1 g/cm3(Predicted)
• LogP: 2.47340

Purity/Quality:

99% ^*data from raw suppliers

Ubrogepant ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Ubrogepant, is a new drug possible used for the treatment of migraine.

Technology Process of Ubrogepant

There total 40 articles about Ubrogepant 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: 95.0%

(S)-2′-oxo-1′,2′,5,7-tetrahydrospiro[cyclopenta[b]pyridine-6,3′-pyrrolo[2,3-b]pyridine]-3-carboxylic acid (1375541-21-1) + (3S,5S,6R)-6-methyl-2-oxo-5-phenyl-1-(2,2,2-trifluoroethyl)piperidin-3-aminium hydrochloride (1375470-88-4) → (6S)-N-[(3S,5S,6R)-6-methyl-2-oxo-5-phenyl-1-(2,2,2-trifluoroethyl)piperidin-3-yl]-2′-oxo-1′,2′,5,7-tetrahydrospiro[cyclopenta[b]pyridine-6,3′-pyrrolo[2,3-b]pyridine]-3-carboxamide (1374248-77-7)

Guidance literature:

(S)-2′-oxo-1′,2′,5,7-tetrahydrospiro[cyclopenta[b]pyridine-6,3′-pyrrolo[2,3-b]pyridine]-3-carboxylic acid; (3S,5S,6R)-6-methyl-2-oxo-5-phenyl-1-(2,2,2-trifluoroethyl)piperidin-3-aminium hydrochloride; With 2-hydroxy-pyridine N-oxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In water; acetonitrile; at 20 ℃; pH=6 - 6.5;

With water; In ethanol;

DOI:10.1021/acs.oprd.7b00293

Reference yield:

(S)-2′-oxo-1′,2′,5,7-tetrahydrospiro[cyclopenta[b]pyridine-6,3′-pyrrolo[2,3-b]pyridine]-3-carboxylic acid (1375541-21-1) + (3S,5S,6R)-6-methyl-2-oxo-5-phenyl-1-(2,2,2-trifluoroethyl)piperidin-3-aminium hydrochloride (1375470-88-4) → (6S)-N-[(3S,5S,6R)-6-methyl-2-oxo-5-phenyl-1-(2,2,2-trifluoroethyl)piperidin-3-yl]-2'-oxo-1',2',5,7-tetrahydrospiro[cyclopenta[b]pyridine-6,3'-pyrrolo[2,3-b]pyridine]-3-carboxamide (1374248-77-7)

Guidance literature:

With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 23 ℃; for 3h;

Reference yield:

3-chlorophenylacetone (14123-60-5) → (6S)-N-[(3S,5S,6R)-6-methyl-2-oxo-5-phenyl-1-(2,2,2-trifluoroethyl)piperidin-3-yl]-2'-oxo-1',2',5,7-tetrahydrospiro[cyclopenta[b]pyridine-6,3'-pyrrolo[2,3-b]pyridine]-3-carboxamide (1374248-77-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: caesium carbonate / N,N-dimethyl-formamide / 0.75 h / 23 °C

1.2: 2.5 h

2.1: acetic acid; sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 28 h / 23 °C / molecular sieves

2.2: 18 h / 23 - 60 °C

2.3: ChiralPak_.(R). AD column / Resolution of racemate

3.1: hydrogen / 10 wt% Pd(OH)2 on carbon / methanol / 16 h / 23 °C

3.2: 2 h / 0 - 23 °C

4.1: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 3 h / 23 °C

With hydrogen; sodium tris(acetoxy)borohydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; caesium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; 10 wt% Pd(OH)2 on carbon; In methanol; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

upstream raw materials:

(S)-1‘-(tert-butyl)-2’-oxo-1‘,2’,5,7-tetrahydrospiro[cyclopenta[b]pyridine-6,3’-pyrrolo[2,3-b]pyridine]-3-carboxylic acid

(S)-2′-oxo-1′,2′,5,7-tetrahydrospiro[cyclopenta[b]pyridine-6,3′-pyrrolo[2,3-b]pyridine]-3-carboxylic acid

(3S,5S,6R)-6-methyl-2-oxo-5-phenyl-1-(2,2,2-trifluoroethyl)piperidin-3-aminium hydrochloride

C₂₃H₂₈ClN₃O₃

Refernces

• 1、 Yasuda, Nobuyoshi,Cleator, Ed,Kosjek, Birgit,Yin, Jianguo,Xiang, Bangping,Chen, Frank,Kuo, Shen-Chun,Belyk, Kevin,Mullens, Peter R.,Goodyear, Adrian,Edwards, John S.,Bishop, Brian,Ceglia, Scott,Belardi, Justin,Tan, Lushi,Song, Zhiguo J.,Dimichele, Lisa,Reamer, Robert,Cabirol, Fabien L.,Tang, Weng Lin,Liu, Guiquan. "Practical Asymmetric Synthesis of a Calcitonin Gene-Related Peptide (CGRP) Receptor Antagonist Ubrogepant". . p. 1851 - 1858. Retrieved 2017/11/24.