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

HRID 2114317Notes

Reaction equation

HRID 2114317 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][C:21]([F:24])=[CH:20][CH:19]=2)[N:12]=1)=[O:10])C.C(OC(=O)[C:29](=[O:34])[CH:30]([C:32]#N)[CH3:31])C.[ClH:36].FC1C=CC(NN)=CC=1.NC1N(C(OC(C)(C)C)=O)N=C(C(OC)=O)C=1.[N:63]1([C:72]2[CH:77]=[CH:76][N:75]=[CH:74][CH:73]=2)[CH2:68][CH2:67][CH:66]([CH2:69][CH2:70][NH2:71])[CH2:65][CH2:64]1>>[N:63]1([C:72]2[CH:77]=[CH:76][N:75]=[CH:74][CH:73]=2)[CH2:68][CH2:67][CH:66]([CH2:69][CH2:70][NH:71][C:9]([C:11]2[C:15]([CH3:16])=[C:14]([NH:17][C:29](=[O:34])[C:30]3[CH:32]=[CH:5][CH:4]=[CH:3][C:31]=3[Cl:36])[N:13]([C:18]3[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=3)[N:12]=2)=[O:10])[CH2:65][CH2:64]1

Participants

7

Reactant 6

HCID 1048PyrazoleHCID 699814-Fluorophenylhydrazine 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 69153527ethyl 5-amino-1-(4-fluorophenyl)-4-methyl-1H-pyrazole-3-carboxylate

Product 1

HCID 597735504-Methyl-5-(2-chloro-benzoylamino)-1-(p-fluorophenyl)-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-(4-fluorophenyl)-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 4-fluorophenylhydrazine 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-b24f9d0012e9451f99538cdade90f2ab
Source dataset
uspto-grants-2008_10
Patent number
US07432379B2

Reaction notes

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