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

HRID 2114309Notes

Reaction equation

HRID 2114309 reaction equation
N1C=CC=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]=[CH:20][CH:19]=2)[N:12]=1)=[O:10])C.C(OC(=O)C(=O)C(C#N)C)C.NC1N(C(OC(C)(C)C)=O)N=C(C(OC)=O)C=1.[F:52][C:53]1[CH:61]=[CH:60][CH:59]=[CH:58][C:54]=1[C:55](Cl)=[O:56].ClC1C=CC=CC=1C(Cl)=O.[N:72]1([C:81]2[CH:86]=[CH:85][N:84]=[CH:83][CH:82]=2)[CH2:77][CH2:76][CH:75]([CH2:78][CH2:79][NH2:80])[CH2:74][CH2:73]1>>[N:72]1([C:81]2[CH:86]=[CH:85][N:84]=[CH:83][CH:82]=2)[CH2:77][CH2:76][CH:75]([CH2:78][CH2:79][NH:80][C:9]([C:11]2[C:15]([CH3:16])=[C:14]([NH:17][C:55](=[O:56])[C:54]3[CH:58]=[CH:59][CH:60]=[CH:61][C:53]=3[F:52])[N:13]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:12]=2)=[O:10])[CH2:74][CH2:73]1

Participants

8

Reactant 7

HCID 1048PyrazoleHCID 98082-Fluorobenzoyl chlorideHCID 691102-Chlorobenzoyl chlorideHCID 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 68887576ethyl 5-amino-4-methyl-1-phenyl-1H-pyrazole-3-carboxylate

Product 1

HCID 597734324-Methyl-5-(2-fluoro-benzoylamino)-1-phenyl-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-4-methyl-1-phenyl-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)) in place of compound 20 and 2-fluorobenzoyl chloride in place compound 21, 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-fe3d465c47654c4a9a52e67773118114
Source dataset
uspto-grants-2008_10
Patent number
US07432379B2

Reaction notes

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