IP Library › Granted Patent US 10,053,466
Granted Patent B2
US 10,053,466 · App. 15/831,895 · Granted Aug 21, 2018

Process for preparing chiral dipeptidyl peptidase-IV inhibitors

Inventors: John Y. L. Chung (Edison, NJ); Feng Peng (Edison, NJ); Yonggang Chen (Westfield, NJ); Amude Mahmoud Kassim (Fairless Hills, PA); Cheng-yi Chen (Princeton, NJ); Mathew Maust (Manville, NJ); Mark McLaughlin (Summit, NJ); Michael J. Zacuto (Jersey City, NJ); Qinghao Chen (Edison, NJ); Lushi Tan (Edison, NJ); Zhiguo Jake Song (Edison, NJ); Yang Cao (Scotch Plains, NJ); Feng Xu (Staten Island, NY)
Assignee: Merck Sharp & Dohme Corp.
C07D487/04A61K31/4162
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Quick Facts
Patent No.
US 10,053,466
App. No.
15/831,895
Granted
Aug 21, 2018
Kind
B2
Abstract

A process for preparing a compound of structural Formula Ia: comprising Boc deprotection with TFA of: and reductive amination of:

Claims (8)

1. A process of preparing a compound of Formula 7

comprising reacting 2,4-difluorobenzaldehyde and nitromethane in the present of a copper salt, ligand, base and solvent to produce a compound of Formula 17:

2. The process of claim 1 further comprising the step of reacting the compound of Formula 17 with acrolein in the presence of a base and solvent to produce a compound of Formula 18:

3. The process of claim 2 further comprising the step of reacting the compound of Formula 18 with a chlorinating agent in the presence of a base and a solvent to produce a compound of Formula 19:

4. The process of claim 3 further comprising the step of crystallizing the compound of Formula 19 under basic conditions to produce a compound of Formula 19t:

5. The process of claim 4 further comprising the steps of reacting the compound of Formula 19t with a hydrobrating agent and an oxidant to produce a compound of Formula 20:

and

reacting the compound of Formula 20 with a reducing agent and a protecting group to produce a compound of Formula 21:

Assignments (3)
MERGER Recorded Aug 8, 2022
From: MERCK SHARP & DOHME CORP.
To: MERCK SHARP & DOHME LLC
Reel/Frame 061102/0145 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 6, 2018
From: CHUNG, JOHN Y.L.; PENG, FENG; CHEN, YONGGANG; KASSIM, AMUDE MAHMOUD; MAUST, MATHEW; MCLAUGHLIN, MARK; CHEN, QINGHAO; TAN, LUSHI; SONG, ZHIGUO JAKE; CAO, YANG; XU, FENG; CHEN, CHENG YI; ZACUTO, MICHAEL J.
To: MERCK SHARP & DOHME CORP.
Reel/Frame 046303/0793 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 13, 2018
From: CHUNG, JOHN Y. L.; PENG, FENG; CHEN, YONGGANG; KASSIM, AMUDE MAHMOUD; CHEN, CHENG-YI; MAUST, MATHEW; MCLAUGHLIN, MARK; ZACUTO, MICHAEL J.; CHEN, QINGHAO; TAN, LUSHI; SONG, ZHIGUO JAKE; CAO, YANG; XU, FENG
To: MERCK SHARP & DOHME CORP.
Reel/Frame 045935/0619 →
Continuity (3)
Division 15325100
Provisional Application 62026763 · Jul 21, 2014
Related Publication 20180093992A1 · Apr 5, 2018