公开(公告)号：US20210078940A1

公开(公告)日：2021-03-18

申请号：US17050255

申请日：2019-04-26

申请人： API CORPORATION

发明人： Masaki NAGAHAMA ,  Hideki OOMIYA ,  Daiki OKADO ,  Hirotsugu TANIIKE

IPC分类号： C07C253/20 ,  C07C51/06

摘要： The present invention provides a method for industrially producing a highly pure aromatic nitrile compound and a highly pure aromatic carboxylic acid compound safely and highly efficiently at low costs. Compound (2) is subjected to Willgerodt reaction in the presence of an additive as necessary, and the obtained amide compound (3) is hydrolyzed and neutralized to give carboxylic acid compound (4). Carboxylic acid compound (4) is reacted with a halogenating agent in the presence of a catalyst as necessary in an organic solvent, and further reacted with an amidating agent, and the obtained amide compound (5) or (6) is reacted with a dehydrating agent to give nitrile compound (1). Alternatively, carboxylic acid compound (4) is reacted with a halogenating agent and a compound represented by the formula R6SO2R7 in the presence of a catalyst as necessary in an organic solvent to give nitrile compound (1). Np is a naphthyl group optionally having substituent(s), R5 is an alkylene group having 1-3 carbon atoms, and other symbols are as described in the DESCRIPTION.

公开(公告)号：US20240351978A1

公开(公告)日：2024-10-24

申请号：US18738245

申请日：2024-06-10

申请人： API CORPORATION

发明人： Masaki NAGAHAMA ,  Hideki OOMIYA ,  Daiki OKADO ,  Hirotsugu TANIIKE

IPC分类号： C07C253/20 ,  C07C51/06 ,  C07C57/38 ,  C07C255/33

CPC分类号： C07C253/20 ,  C07C51/06 ,  C07C57/38 ,  C07C255/33 ,  C07C2602/10

摘要： The present invention provides a method for industrially producing a highly pure aromatic nitrile compound and a highly pure aromatic carboxylic acid compound safely and highly efficiently at low costs. Compound (2) is subjected to Willgerodt reaction in the presence of an additive as necessary, and the obtained amide compound (3) is hydrolyzed and neutralized to give carboxylic acid compound (4). Carboxylic acid compound (4) is reacted with a halogenating agent in the presence of a catalyst as necessary in an organic solvent, and further reacted with an amidating agent, and the obtained amide compound (5) or (6) is reacted with a dehydrating agent to give nitrile compound (1). Alternatively, carboxylic acid compound (4) is reacted with a halogenating agent and a compound represented by the formula R6SO2R7 in the presence of a catalyst as necessary in an organic solvent to give nitrile compound (1). Np is a naphthyl group optionally having substituent(s), R5 is an alkylene group having 1-3 carbon atoms, and other symbols are as described in the DESCRIPTION.

公开(公告)号：US20240002340A1

公开(公告)日：2024-01-04

申请号：US18243409

申请日：2023-09-07

申请人： API CORPORATION

发明人： Masato MURAI ,  Jun TAKEHARA ,  Daiki OKADO

IPC分类号： C07D211/60

CPC分类号： C07D211/60

摘要： A method for producing a compound represented by the formula (1):




wherein LG is a leaving group, PG1 is an amino-protecting group, and R is a hydrocarbon group having 1-8 carbon atoms and optionally having substituent(s), comprising



reacting a compound represented by the formula (6):








with an amino group protecting agent to obtain a compound represented by the formula (7):




or a salt thereof;



reacting the aforementioned compound represented by the formula (7) with a lactonization agent to obtain a compound represented by the formula (8):










reacting the aforementioned compound represented by the formula (8) with an esterification agent to obtain a compound represented by the formula (9):








and



reacting the aforementioned compound represented by the formula (9) with a leaving group introduction agent.

公开(公告)号：US20220281806A1

公开(公告)日：2022-09-08

申请号：US17824393

申请日：2022-05-25

申请人： API CORPORATION

发明人： Masaki NAGAHAMA ,  Daiki OKADO ,  Hirotsugu TANIIKE

IPC分类号： C07C253/22

摘要： The present invention provides high purity 2-naphthylacetonitrile with fewer impurities that is useful as a starting material or intermediate for the synthesis of various pharmaceutical products, agricultural chemicals, and chemical products, and a production method thereof. A high purity 2-naphthylacetonitrile having an HPLC purity of 2-naphthylacetonitrile of not less than 95 area %, and containing naphthalene compounds represented by the formulas (a)-(j) at a content of a predetermined area % or below. A method for producing high purity 2-naphthylacetonitrile, including the following step 1 and step 2: step 1: a step of subjecting 2′-acetonaphthone to a Willgerodt reaction in the presence of an additive where necessary, and hydrolyzing the obtained amide compound to give 2-naphthylacetic acid; step 2: a step of reacting the 2-naphthylacetic acid obtained in step 1, a halogenating agent and sulfamide in the presence of a catalyst as necessary in an organic solvent to give 2-naphthylacetonitrile.

公开(公告)号：US20220009880A1

公开(公告)日：2022-01-13

申请号：US17295222

申请日：2020-10-28

申请人： API CORPORATION

发明人： Masaki NAGAHAMA ,  Daiki OKADO ,  Hirotsugu TANIIKE

IPC分类号： C07C253/22

摘要： High purity 2-naphthylacetonitrile with fewer impurities can be used as a starting material or intermediate for synthesizing various pharmaceutical products, agricultural chemicals, and chemical products, and a production method thereof. A high purity 2-naphthylacetonitrile having an HPLC purity of 2-naphthylacetonitrile of not less than 95 area %, and containing naphthalene compounds represented by the formulas (a)-(j) at a content of a predetermined area % or below. A method for producing high purity 2-naphthylacetonitrile, may include: subjecting 2′-acetonaphthone to a Willgerodt reaction in the presence of an additive where necessary, and hydrolyzing the obtained amide compound to give 2-naphthylacetic acid; and reacting the 2-naphthylacetic acid obtained in the subjecting, a halogenating agent and sulfamide in the presence of a catalyst as necessary in an organic solvent to give 2-naphthylacetonitrile.

公开(公告)号：US20240150292A1

公开(公告)日：2024-05-09

申请号：US18390624

申请日：2023-12-20

申请人： API CORPORATION

发明人： Masato MURAI ,  Jun TAKEHARA ,  Daiki OKADO

IPC分类号： C07D211/60

CPC分类号： C07D211/60

摘要： The present invention aims to provide a method for producing a (2S,5R)-5-(protected oxyamino)-piperidine-2-carboxylic acid derivative at a low cost that can be performed under mild reaction conditions not requiring a facility at an extremely low temperature, is safer, can control the quality of the desired product with ease, and shows good workability in the site of production. A method for producing a compound represented by the formula (2)




wherein PG1 is an amino-protecting group, PG2 is an amino-protecting group, PG3 is a hydroxyl-protecting group, LG is a leaving group, and R is a hydrocarbon group having 1-8 carbon atoms and optionally having substituent(s), including a step of reacting a compound represented by the formula (1):




wherein each symbol is as defined above, with a hydroxylamine derivative represented by the formula PG2NHOPG3 wherein each symbol is as defined above, in the presence of a base in a solvent.

公开(公告)号：US20230227400A1

公开(公告)日：2023-07-20

申请号：US18190244

申请日：2023-03-27

申请人： API CORPORATION

发明人： Masaki NAGAHAMA ,  Daiki OKADO ,  Hirotsugu TANIIKE

IPC分类号： C07C253/22

CPC分类号： C07C253/22

摘要： High purity 2-naphthylacetonitrile with fewer impurities that is useful as a starting material or intermediate for the synthesis of various pharmaceutical products, agricultural chemicals, and chemical products, and a production method thereof. A high purity 2-naphthylacetonitrile having an HPLC purity of 2-naphthylacetonitrile of not less than 95 area %, and containing naphthalene compounds represented by the formulas (a)-(j) at a content of a predetermined area % or below. A method for producing high purity 2-naphthylacetonitrile.

公开(公告)号：US20210403427A1

公开(公告)日：2021-12-30

申请号：US17277456

申请日：2019-09-24

申请人： API CORPORATION

发明人： Masato MURAI ,  Jun TAKEHARA ,  Daiki OKADO

IPC分类号： C07D211/60

摘要： The present invention aims to provide a method for producing a (2S,5R)-5-(protected oxyamino)-piperidine-2-carboxylic acid derivative at a low cost that can be performed under mild reaction conditions not requiring a facility at an extremely low temperature, is safer, can control the quality of the desired product with ease, and shows good workability in the site of production. A method for producing a compound represented by the formula (2): wherein PG1 is an amino-protecting group, PG2 is an amino-protecting group, PG3 is a hydroxyl-protecting group, LG is a leaving group, and R is a hydrocarbon group having 1-8 carbon atoms and optionally having substituent(s), including a step of reacting a compound represented by the formula (1): wherein each symbol is as defined above, with a hydroxylamine derivative represented by the formula PG2NHOPG3 wherein each symbol is as defined above, in the presence of a base in a solvent.