249889-69-8

Basic information

• Product Name: 1,5-Naphthyridin-4-amine,6-methoxy-(9CI)
• Synonyms: 1,5-Naphthyridin-4-amine,6-methoxy-(9CI);6-Methoxy-1,5-naphthyridin-4-amine;6-Methoxy-[1,5]naphthyridin-4-ylamine
• CAS NO: 249889-69-8
• Molecular Formula: C₉H₉N₃O
• Molecular Weight: 175.18726
• Product Categories: METHOXY
• Mol File: 249889-69-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,5-Naphthyridin-4-amine,6-methoxy-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1,5-Naphthyridin-4-amine,6-methoxy-(9CI)(249889-69-8)
• EPA Substance Registry System: 1,5-Naphthyridin-4-amine,6-methoxy-(9CI)(249889-69-8)

Safety Data

• Hazardous Substances Data: 249889-69-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1,5-Naphthyridin-4-amine,6-methoxy-(9CI) is used as a building block for the development of novel drugs due to its unique structure and properties. It is involved in the synthesis of new molecules with potential biological activity, making it a valuable component in drug discovery and design.
Used in Agrochemical Industry:
1,5-Naphthyridin-4-amine,6-methoxy-(9CI) is also used as a building block in the development of new agrochemicals. Its unique structure and properties contribute to the creation of innovative compounds with potential applications in agriculture, such as pesticides or herbicides.
Used in Chemical Research:
1,5-Naphthyridin-4-amine,6-methoxy-(9CI) is utilized in chemical research for the study and development of new chemical compounds. Its unique structure allows for exploration of its potential applications and interactions with other molecules, contributing to the advancement of chemical science.
Used as a Potential Therapeutic Agent:
1,5-Naphthyridin-4-amine,6-methoxy-(9CI) has been studied as a potential therapeutic agent for various diseases and disorders. Its unique properties and structure make it a promising candidate for further research and development in the field of medicine.

Upstream product

• 394223-86-0 6-methoxy-1,5-naphthyridin-4-yl trifluoromethanesulfonate 

Downstream Products

• 877457-36-8 C₂₂H₃₀N₄O₄ 
• 615568-05-3 C₂₁H₂₈N₄O₄ 
• 615568-44-0 (R/S)-4-tert-butoxycarbonylamino-cyclohex-1-enecarboxylic acid (6-methoxy-[1,5]naphthyridin-4-yl)-amide 

Relevant articles and documents

Flexible palladium-catalysed amidation reactions for the synthesis of complex aryl amides

This Letter describes the synthesis of complex aryl amides using palladium-catalysed amidation reactions. Use of these conditions allowed for the coupling of a variety of aryl halides and triflates with a host of primary amides in high yields.

NOVEL COMPOUNDS HAVING AN ANTI-BACTERIAL ACTIVITY

The present invention describes novel anti-bacterial compounds of formula (I). These compounds are, amongst others, of interest as inhibitors of DNA gyrase.

AMINOPIPERIDINE DERIVATIVES AS ANTIBACTERIALS

From EXEMP_CLAIMS : 1. A compound of formula (I) or a pharmaceutically acceptable N-oxide, salt or ester thereof: wherein: either Z1, Z2, Z3, Z4 and Z5 are CR1a; or one of Z1, Z2, Z3, Z4 and Z5 is N, and the remainder are CR1a; R1 and R1a are independently hydrogen; hydroxy; (C1-6)alkoxy optionally substituted by (C1-6)alkoxy, amino, piperidyl, guanidino or amidino optionally N-substituted by one or two (C1-6)alkyl, acyl or (C1-6)alkylsulphonyl groups, CONH2, hydroxy, thiol, (C1-6)alkylthio, heterocyclylthio, heterocyclyloxy, arylthio, aryloxy, acylthio, acyloxy or (C1-6)alkylsulphonyloxy; (C1-6)alkoxy-substituted (C1-6)alkyl; halogen; (C1-6)alkyl; (C1-6)alkylthio; nitro; azido; acyl; acyloxy; (C1-6)alkylsulphonyl; (C1-6)alkylsulphoxide; arylsulphonyl; arylsulphoxide or an amino, piperidyl, guanidino or amidino group optionally N-substituted by one or two (C1-6)alkyl, acyl or (C1-6)alkylsulphonyl groups; and additionally when Z5 is CR1a, R1a may be (C1-4)alkyl-CO2H or (C1-4)alkyl-CONH2 in which the (C1-4) alkyl is substituted by R12; (C1-4)alkyl substituted by cyano, amino or guanidino; aminocarbonyl optionally substituted by hydroxy, (C1-6)alkyl, hydroxy(C1-6)alkyl, aminocarbonyl(C1-6)alkyl, (C2-6)alkenyl, (C1-6)alkylsulphonyl, trifluoromethylsulphonyl, (C2-6)alkenylsulphonyl, (C1-6)alkoxycarbonyl, (C1-6)alkylcarbonyl, (C2-6)alkenyloxycarbonyl, (C2-6)alkenylcarbonyl, or CH(R13)CO2H or CH(R13)CONH2 optionally further substituted by (C1-6)alkyl, hydroxy(C1-6)alkyl, aminocarbonyl(C1-6)alkyl or (C2-6)alkenyl; hydroxy(C1-6)alkyl; carboxy; cyano or (C1-6)alkoxycarbonyl; wherein R13 is a natural α-amino acid side chain or its enantiomer; provided that when Z1, Z2, Z3, Z4 and Z5 are CR1a, then R1 is not hydrogen; R2 is hydrogen, or (C1-4)alkyl or (C2-4)alkenyl optionally substituted with 1 to 3 groups selected from: amino optionally substituted by one or two (C1-4)alkyl groups; carboxy; (C1-4)alkoxycarbonyl; (C1-4)alkylcarbonyl; (C2-4)alkenyloxycarbonyl; (C2-4)alkenylcarbonyl; aminocarbonyl wherein the amino group is optionally substituted by hydroxy, (C1-4)alkyl, hydroxy(C1-4)alkyl, aminocarbonyl(C1-4)alkyl, (C2-4)alkenyl, (C1-4)alkylsulphonyl, trifluoromethylsulphonyl, (C2-4)alkenylsulphonyl, (C1-4)alkoxycarbonyl, (C1-4)alkylcarbonyl, (C2-4)alkenyloxycarbonyl or (C2-4)alkenylcarbonyl; cyano; tetrazolyl; 2-oxo-oxazolidinyl optionally substituted by R10; 3-hydroxy-3-cyclobutene-1,2-dione-4-yl; 2,4-thiazolidinedione-5-yl; tetrazol-5-ylaminocarbonyl; 1,2,4-triazol-5-yl optionally substituted by R10; 5-oxo-1,2,4-oxadiazol-3-yl; thiol; halogen; (C1-4)alkylthio; trifluoromethyl; azido; hydroxy optionally substituted by (C 1-4)alkyl, (C2-4)alkenyl, (C1-4)alkoxycarbonyl, (C1-4)alkylcarbonyl, (C2-4)alkenyloxycarbonyl, (C2-4)alkenylcarbonyl; oxo; (C1-4)alkylsulphonyl; (C2-4)alkenylsulphonyl; or (C1-4)aminosulphonyl wherein the amino group is optionally substituted by (C1-4)alkyl or (C2-4)alkenyl; R3 is hydrogen; or R3 is in the 2-, 3- or 4-position and is: carboxy; (C1-6)alkoxycarbonyl; aminocarbonyl wherein the amino group is optionally substituted by hydroxy, (C1-6)alkyl, hydroxy(C1-6)alkyl, aminocarbonyl(C1-6)alkyl, (C2-6)alkenyl, (C1-6)alkylsulphonyl, trifluoromethylsulphonyl, (C1-6)alkenylsulphonyl, (C1-6)alkoxycarbonyl, (C1-6)alkylcarbonyl, (C2-6)alkenyloxycarbonyl or (C2-6)alkenylcarbonyl and optionally further substituted by (C1-6)alkyl, hydroxy(C1-6)alkyl, aminocarbonyl(C1-6)alkyl or (C2-6)alkenyl; cyano; tetrazolyl; 2-oxo-oxazolidinyl optionally substituted by R10; 3-hydroxy-3-cyclobutene-1,2-dione-4-yl; 2,4-thiazolidinedione-5-yl; tetrazol-5-ylaminocarbonyl; 1,2,4-triazol-5-yl optionally substituted by R10; or 5-oxo-1,2,4-oxadiazol-3-yl; or (C 1-4)alkyl optionally substituted, or ethenyl substituted, with any of the substituents listed above for R3 and up to 3 groups R12 independently selected from: thiol; halogen; (C1-6)alkylthio; trifluoromethyl; azido; (C1-6)alkoxycarbonyl; (C1-6)alkylcarbonyl; (C2-6)alkenyloxycarbonyl; (C2-6)alkenylcarbonyl; hydroxy optionally substituted by (C1-6)alkyl, (C2-6)alkenyl, (C1-6)alkoxycarbonyl, (C1-6)alkylcarbonyl, (C2-6)alkenyloxycarbonyl, (C2-6)alkenylcarbonyl or aminocarbonyl wherein the amino group is optionally substituted by (C1-6)alkyl, (C2-6)alkenyl, (C1-6)alkylcarbonyl or (C2-6)alkenylcarbonyl; amino optionally mono- or disubstituted by (C1-6)alkoxycarbonyl, (C1-6)alkylcarbonyl, (C2-6)alkenyloxycarbonyl, (C2-6)alkenylcarbonyl, (C1-6)alkyl, (C2-6)alkenyl, (C1-6)alkylsulphonyl, (C2-6)alkenylsulphonyl or aminocarbonyl wherein the amino group is optionally substituted by (C1-6)alkyl or (C2-6)alkenyl; aminocarbonyl wherein the amino group is optionally substituted by (C1-6)alkyl, hydroxy(C1-6)alkyl, aminocarbonyl(C1-6)alkyl, (C2-6)alkenyl, (C1-6)alkoxycarbonyl, (C1-6)alkylcarbonyl, (C2-6)alkenyloxycarbonyl or (C2-6)alkenylcarbonyl and optionally further substituted by (C 1-6)alkyl, hydroxy(C1-6)alkyl, aminocarbonyl(C1-6)alkyl or (C2-6)alkenyl; oxo; (C1-6)alkylsulphonyl; (C2-6)alkenylsulphonyl; or (C1-6)aminosulphonyl wherein the amino group is optionally substituted by (C1-6)alkyl or (C2-6)alkenyl; in addition when R3 is disubstituted with a hydroxy or amino containing substituent and carboxy containing substituent these may together form a cyclic ester or amide linkage, respectively; or when R3 is in the 3- or 4-position it may with R2 or R4 form a C3-5 alkylene group optionally substituted by a group R5 selected from: (C1-12)alkyl; hydroxy(C1-12)alkyl; (C1-12)alkoxy(C1-12)alkyl; (C1-12)alkanoyloxy(C1-12)alkyl; (C3-6)cycloalkyl; hydroxy(C3-6)cycloalkyl; (C1-12)alkoxy(C3-6)cycloalkyl; (C1-12)alkanoyloxy(C3-6)cycloalkyl; (C3-6)cycloalkyl(C1-12)alkyl; hydroxy-, (C1-12)alkoxy- or (C1-12)alkanoyloxy-(C3-6)cycloalkyl(C1-12)alkyl; cyano; cyano(C1-12)alkyl; (C2-12)alkenyl; (C2-12)alkynyl; tetrahydrofuryl; mono- or di-(C1-12)alkylamino(C1-12)alkyl; acylamino(C1-12)alkyl; (C1-12)alkyl- or acyl-aminocarbonyl(C1-12)alkyl; mono- or di-(C1-12)alkylamino(hydroxy) (C1-12)alkyl; optionally substituted phenyl(C1-12)alkyl, phenoxy(C1-12)alkyl or phenyl(hydroxy)(C1-12)alkyl; optionally substituted diphenyl(C1-12)alkyl; optionally substituted phenyl(C2-12)alkenyl; optionally substituted benzoyl or benzoyl(C1-12)alkyl; optionally substituted heteroaryl or heteroaryl(C1-12)alkyl; and optionally substituted heteroaroyl or heteroaroyl(C1-12)alkyl; R4 forms a group with R3 as above defined, or is a group -CH2-R5 where R5 is as defined above: n is 0, 1 or 2; A is NR11 or CR6R7 and B is NR11, O, SO2 or CR8R9 and wherein: each of R6, R7, R8 and R9 is independently selected from: hydrogen; (C1-6)alkylthio; halo; trifluoromethyl; azido; (C1-6)alkyl; (C2-6)alkenyl; (C1-6)alkoxycarbonyl; (C1-6)alkylcarbonyl; (C2-6)alkenyloxycarbonyl; (C2-6)alkenylcarbonyl; hydroxy, amino or aminocarbonyl optionally substituted as for corresponding substituents R12 in R3; (C1-6)alkylsulphonyl; (C2-6)alkenylsulphonyl; or aminosulphonyl wherein the amino group is optionally substituted by (C1-6)alkyl or (C1-6)alkenyl; or R6 and R8 together represent a bond and R7 and R9 are as above defined; or R6 and R7 or R8 and R9 together represent oxo; provided that: when A is NR11, B is not NR11, O or SO2; when A is CO, B is not CO, O or SO2; when n is 0 and A is NR11, CR8R9 can only be CO; when A is CR6R7 and B is SO2, n is 0; when n is 0, B is not NR11 or O; and when A-B is CR7=CR9, n is 1 or 2; R10 is selected from (C1-4)alkyl; (C2-4)alkenyl and aryl any of which may be optionally substituted by a group R12 as defined above; carboxy; aminocarbonyl wherein the amino group is optionally substituted by hydroxy, (C1-6)alkyl, (C2-6)alkenyl, (C1-6)alkylsulphonyl, trifluoromethylsulphonyl, (C2-6)alkenylsulphonyl, (C1-6)alkoxycarbonyl, (C1-6)alkylcarbonyl, (C2-6)alkenyloxycarbonyl or (C2-6)alkenylcarbonyl and optionally further substituted by (C1-6)alkyl or (C2-6)alkenyl; (C1-6)alkylsulphonyl; trifluoromethylsulphonyl; (C2-6)alkenylsulphonyl; (C1-6)alkoxycarbonyl; (C1-6)alkylcarbonyl; (C2-6)alkenyloxycarbonyl; and (C2-6)alkenylcarbonyl; R11 is hydrogen; trifluoromethyl, (C1-6)alkyl; (C2-6)alkenyl; (C1-6)alkoxycarbonyl; (C1-6)alkylcarbonyl; aminocarbonyl wherein the amino group is optionally substituted by (C1-6)alkoxycarbonyl, (C1-6)alkylcarbonyl, (C2-6)alkenyloxycarbonyl, (C2-6)alkenylcarbonyl, (C1-6)alkyl or (C2-6)alkenyl and optionally further substituted by (C1-6)alkyl or (C2-6)alkenyl; wherein optionally substituted phenyl, benzoyl, heteroaryl and heteroaroyl groups are optionally substituted with up to five groups selected from halogen, mercapto, (C1-6)alkyl, phenyl, (C1-6)alkoxy, hydroxy(C1-6)alkyl, mercapto (C1-6)alkyl, halo(C1-6)alkyl, hydroxy, amino, nitro, carboxy, (C1-6)alkylcarbonyloxy, (C1-6)alkoxycarbonyl, formyl, and (C1-6)alkylcarbonyl groups.

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