Pyrazole → 4-Methyl-5-(2-chloro-benzoylamino)-1-(3-methoxyphenyl)-pyrazole-3-carboxylic acid[2-(3,4,5,6-tetrahydro-2h-[1,4']bipyridin-4-yl)-ethyl]amide

HRID 2220764Notes

Reaction equation

HRID 2220764 reaction equation
N1C=[CH:4][CH:3]=N1.C(OC([C:11]1[C:15](C)=[C:14](N)[N:13]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20](OC)C=2)[N:12]=1)=O)C.C(OC(=O)C(=O)C(C#N)C)C.Cl.[CH3:38][O:39][C:40]1[CH:41]=[C:42]([NH:46][NH2:47])[CH:43]=[CH:44][CH:45]=1.NC1N(C(OC(C)(C)C)=O)N=C(C(OC)=O)C=1.O=[C:66]1NC2C=CC=CC=2C(C2C=CC=CC=2)=N[CH:67]1[NH:83][C:84]([C:86]1[C:90]([CH3:91])=[C:89]([NH:92][C:93](=[O:101])[C:94]2[CH:99]=[CH:98][CH:97]=[CH:96][C:95]=2[Cl:100])N(C2C=CC=CN=2)N=1)=[O:85]>>[N:13]1([C:14]2[CH:15]=[CH:11][N:12]=[CH:4][CH:3]=2)[CH2:18][CH2:23][CH:22]([CH2:66][CH2:67][NH:83][C:84]([C:86]2[C:90]([CH3:91])=[C:89]([NH:92][C:93](=[O:101])[C:94]3[CH:99]=[CH:98][CH:97]=[CH:96][C:95]=3[Cl:100])[N:46]([C:42]3[CH:43]=[CH:44][CH:45]=[C:40]([O:39][CH3:38])[CH:41]=3)[N:47]=2)=[O:85])[CH2:21][CH2:20]1

Participants

7

Reactant 6

HCID 1048PyrazoleHCID 27239403-Methoxyphenylhydrazine hydrochlorideHCID 59223396Ethyl 3-cyano-3-methyl-2-oxopropanoateHCID 597733355-Amino-1-tert-butoxycarbonyl-3-methoxycarbonylpyrazoleHCID 598122274-Methyl-5-(2-chloro-benzoylamino)-1-(pyridine-2-yl)-pyrazole-3-carboxylic acid(2-oxo-5-phenyl-2,3-dihydro-1h-benzo[e][1,4]diazepin-3-yl)amideHCID 691522355-amino-1-(3-methoxyphenyl)-4-methyl-1H-pyrazole-3-carboxylic acid ethyl ester

Product 1

HCID 597734924-Methyl-5-(2-chloro-benzoylamino)-1-(3-methoxyphenyl)-pyrazole-3-carboxylic acid[2-(3,4,5,6-tetrahydro-2h-[1,4']bipyridin-4-yl)-ethyl]amide

Procedure

The pyrazole acid, prepared as described in Procedure 8 using 5-amino-1-(3-methoxyphenyl)-4-methyl-1H-pyrazole-3-carboxylic acid ethyl ester (prepared as described in Procedure 41 using 3-cyano-3-methyl-2-oxopropanoic acid ethyl ester (U.S. Pat. No. 4,652,669) and 3-methoxyphenylhydrazine hydrochloride) in place of compound 20, was coupled to 2-(3,4,5,6-tetrahydro-2H-[1,4′]bipyridin-4-yl)ethylamine (prepared as described in Procedure 14) using the method of Procedure 10.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-cb77f705c00e436b96796fec4e331aa3
Source dataset
uspto-grants-2008_08
Patent number
US07417152B2

Reaction notes

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