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 2114316Notes

Reaction equation

HRID 2114316 reaction equation
N1[CH:5]=[CH:4][CH:3]=N1.C(O[C:9]([C:11]1[C:15]([CH3:16])=[C:14]([NH2:17])[N:13]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[CH:19]=2)[N:12]=1)=[O:10])C.C(OC(=O)[C:30](=[O:35])[CH:31]([C:33]#N)[CH3:32])C.[ClH:37].COC1C=C(NN)C=CC=1.NC1N(C(OC(C)(C)C)=O)N=C(C(OC)=O)C=1.[N:65]1([C:74]2[CH:79]=[CH:78][N:77]=[CH:76][CH:75]=2)[CH2:70][CH2:69][CH:68]([CH2:71][CH2:72][NH2:73])[CH2:67][CH2:66]1>>[N:65]1([C:74]2[CH:79]=[CH:78][N:77]=[CH:76][CH:75]=2)[CH2:70][CH2:69][CH:68]([CH2:71][CH2:72][NH:73][C:9]([C:11]2[C:15]([CH3:16])=[C:14]([NH:17][C:30](=[O:35])[C:31]3[CH:33]=[CH:5][CH:4]=[CH:3][C:32]=3[Cl:37])[N:13]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[CH:19]=3)[N:12]=2)=[O:10])[CH2:67][CH2:66]1

Participants

7

Reactant 6

HCID 1048PyrazoleHCID 27239403-Methoxyphenylhydrazine hydrochlorideHCID 220278212-[1-(Pyridin-4-yl)piperidin-4-yl]ethan-1-amineHCID 59223396Ethyl 3-cyano-3-methyl-2-oxopropanoateHCID 597733355-Amino-1-tert-butoxycarbonyl-3-methoxycarbonylpyrazoleHCID 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-a00da2eb315d4500bb10c81d7a35f3b1
Source dataset
uspto-grants-2008_10
Patent number
US07432379B2

Reaction notes

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