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EP-3599854-B1 - PYRROLIDINONES AND A PROCESS TO PREPARE THEM

EP3599854B1EP 3599854 B1EP3599854 B1EP 3599854B1EP-3599854-B1

Inventors

  • CHEN, YUZHONG

Dates

Publication Date
20260506
Application Date
20180316

Claims (6)

  1. A compound of Formula II and salts thereof wherein A 1 is CCF 3 , A 2 is CH and A 3 is CH; or A 1 is CH, A 2 is CCF 3 and A 3 is CH; or A 1 is N, A 2 is CCF 3 and A 3 is CH; or A 1 is CCH 3 , A 2 is N and A 3 is COCHF 2 ; R 1 is C 1 -C 4 alkyl; and R 2 is H or C 1 -C 4 alkyl.
  2. A compound of Claim 1 and salts thereof wherein R 1 is methyl, ethyl or propyl; and R 2 is H or methyl.
  3. A compound of Claim 2 and salts thereof selected from the group consisting of methyl (3 R ,4 S )-1-methyl-2-oxo-4-[3-(trifluoromethyl)phenyl]-3-pyrrolidinecarboxylate; and (3 R ,4 S )-1-methyl-2-oxo-4-[3-(trifluoromethyl)phenyl]-3-pyrrolidinecarboxylic acid.
  4. A process for preparing a compound of Formula II-A wherein A 1 is CCF 3 , A 2 is CH and A 3 is CH; or A 1 is CH, A 2 is CCF 3 and A 3 is CH; or A 1 is N, A 2 is CCF 3 and A 3 is CH; or A 1 is CCH 3 , A 2 is N and A 3 is COCHF 2 ; R 1 is C 1 -C 4 alkyl; and R 2 is H comprising alkylating a compound of Formula III wherein A 1 is CCF 3 , A 2 is CH and A 3 is CH; or A 1 is CH, A 2 is CCF 3 and A 3 is CH; or A 1 is N, A 2 is CCF 3 and A 3 is CH; or A 1 is CCH 3 , A 2 is N and A 3 is COCHF 2 with an alkylating agent.
  5. The process of Claim 4 wherein R 1 is C 1 -C 4 alkyl; comprising alkylating a compound of Formula III wherein the alkylating agent is a dialkylsulfate.
  6. The process of Claim 4, wherein R 1 is methyl, ethyl or propyl; and the alkylating agent comprises a dialkylsulfate.

Description

FIELD OF THE INVENTION This invention relates to certain pyrrolidinones of Formula II as defined in claim 1 and methods for preparing a compound of Formula II-A as defined in claim 4. BACKGROUND OF THE INVENTION WO 2015/084796, US 2016/297756 A1, WO 2016/196019 A1 and WO 2016/196593 disclose a variety of substituted cyclic amides, a method using them as a herbicide, and methods to prepare them. WO 2016/094117 discloses certain 3-oxo-3-(arylamino)propanoates, their salts and compositions, a process to prepare them and their use in preparing certain pyrrolidinones useful as herbicides. The pyrrolidinones and a process to prepare them of the present invention are not disclosed in these publications. SUMMARY OF THE INVENTION This application is directed to a compound of Formula II and salts thereof wherein A1 is CCF3, A2 is CH and A3 is CH; orA1 is CH, A2 is CCF3 and A3 is CH; orA1 is N, A2 is CCF3 and A3 is CH; orA1 is CCH3, A2 is N and A3 is COCHF2;R1 is C1-C4 alkyl; andR2 is H or C1-C4 alkyl. This application is also directed to a process for preparing a compound of Formula II-A wherein A1 is CCF3, A2 is CH and A3 is CH; orA1 is CH, A2 is CCF3 and A3 is CH; orA1 is N, A2 is CCF3 and A3 is CH; orA1 is CCH3, A2 is N and A3 is COCHF2;R1 is C1-C4 alkyl; andR2 is H comprising alkylating a compound of Formula III wherein A1 is CCF3, A2 is CH and A3 is CH; orA1 is CH, A2 is CCF3 and A3 is CH; orA1 is N, A2 is CCF3 and A3 is CH; orA1 is CCH3, A2 is N and A3 is COCHF2with an alkylating agent. Formula II-B corresponds to Formula II wherein R2 is C1-C4 alkyl. A compound of Formula II-B wherein A1 is CCF3, A2 is CH and A3 is CH; orA1 is CH, A2 is CCF3 and A3 is CH; orA1 is N, A2 is CCF3 and A3 is CH; orA1 is CCH3, A2 is N and A3 is COCHF2;R1 is C1-C4 alkyl; andR2 is C1-C4 alkyl may be prepared by a process (referred to as "Method D" below) comprising reducing a compound of Formula IV wherein A1 is CCF3, A2 is CH and A3 is CH; orA1 is CH, A2 is CCF3 and A3 is CH; orA1 is N, A2 is CCF3 and A3 is CH; orA1 is CCH3, A2 is N and A3 is COCHF2;R1 is C1-C4 alkyl;each R3a and R3b is independently C1-C4 alkyl; andR4 is substituted or unsubstituted benzylwith a reducing agent. A compound of Formula IV wherein A1 is CCF3, A2 is CH and A3 is CH; orA1 is CH, A2 is CCF3 and A3 is CH; orA1 is N, A2 is CCF3 and A3 is CH; orA1 is CCH3, A2 is N and A3 is COCHF2;R1 is C1-C4 alkyl;each R3a and R3b is independently C1-C4 alkyl; andR4 is substituted or unsubstituted benzyl may be prepared by a process (referred to as "Method E" below) comprising reacting a compound of Formula V or a salt thereof wherein A1 is CCF3, A2 is CH and A3 is CH; orA1 is CH, A2 is CCF3 and A3 is CH; orA1 is N, A2 is CCF3 and A3 is CH; orA1 is CCH3, A2 is N and A3 is COCHF2;R1 is C1-C4 alkyl; andR4 is substituted or unsubstituted benzylwith a di-(C1-C4 alkyl) malonate. Formula II-A corresponds to Formula II wherein R2 is H and may be used to prepare a compound of Formula I. A compound of Formula I wherein A1 is CCF3, A2 is CH and A3 is CH; orA1 is CH, A2 is CCF3 and A3 is CH; orA1 is N, A2 is CCF3 and A3 is CH; orA1 is CCH3, A2 is N and A3 is COCHF2;R1 is C1-C4 alkyl;B1 is CF, B2 is CH and B3 is CH; orB1 is CF, B2 is CF and B3 is CH; orB1 is CF, B2 is N and B3 is CF may be prepared by a process (referred to as "Method F" below) comprising contacting a compound of Formula II-A prepared by the process as described in the Summary of the Invention for preparing a compound of Formula II-Awherein A1 is CCF3, A2 is CH and A3 is CH; orA1 is CH, A2 is CCF3 and A3 is CH; orA1 is N, A2 is CCF3 and A3 is CH; orA1 is CCH3, A2 is N and A3 is COCHF2;R1 is C1-C4 alkyl; andR2 is Hwith a compound of Formula VI wherein B1 is CF, B2 is CH and B3 is CH; orB1 is CF, B2 is CF and B3 is CH; orB1 is CF, B2 is N and B3 is CF. Formula II-B corresponds to Formula II wherein R2 is C1-C4 alkyl and may be used to prepare a compound of Formula I. A compound of Formula I wherein A1 is CCF3, A2 is CH and A3 is CH; orA1 is CH, A2 is CCF3 and A3 is CH; orA1 is N, A2 is CCF3 and A3 is CH; orA1 is CCH3, A2 is N and A3 is COCHF2;R1 is C1-C4 alkyl;B1 is CF, B2 is CH and B3 is CH; orB1 is CF, B2 is CF and B3 is CH; orB1 is CF, B2 is N and B3 is CF may be prepared by a process (referred to as "Method G" below) comprising contacting a compound of Formula II-B prepared by the process as described in Method D for preparing a compound of Formula II-B wherein A1 is CCF3, A2 is CH and A3 is CH; orA1 is CH, A2 is CCF3 and A3 is CH; orA1 is N, A2 is CCF3 and A3 is CH; orA1 is CCH3, A2 is N and A3 is COCHF2;R1 is C1-C4 alkyl; andR2 is C1-C4 alkylwith a compound of Formula VI wherein B1 is CF, B2 is CH and B3 is CH; orB1 is CF, B2 is CF and B3 is CH; orB1 is CF, B2 is N and B3 is CF. DETAILS OF THE INVENTION As used herein, the terms "comprises," "comprising," "includes," "including," "has," "having," "contains", "containing," "characterized by" or any other variation thereof, are intended to cover a non-exclu