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

HRID 2220766Notes

Reaction equation

HRID 2220766 reaction equation
N1C=C[CH:3]=N1.C(OC(C1C(C)=C(N)N([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)N=1)=O)C.C(O[C:27](=O)[C:28](=O)[CH:29]([C:31]#[N:32])C)C.N[C:36]1[N:40]([C:41](OC(C)(C)C)=O)N=[C:38]([C:48](OC)=O)[CH:37]=1.O=[C:53]1NC2C=CC=CC=2C(C2C=CC=CC=2)=N[CH:54]1[NH:70][C:71]([C:73]1[C:77]([CH3:78])=[C:76]([NH:79][C:80](=[O:88])[C:81]2[CH:86]=[CH:85][CH:84]=[CH:83][C:82]=2[Cl:87])[N:75](C2C=CC=CN=2)[N:74]=1)=[O:72]>>[N:40]1([C:28]2[CH:27]=[CH:3][N:32]=[CH:31][CH:29]=2)[CH2:36][CH2:37][CH:38]([CH2:53][CH2:54][NH:70][C:71]([C:73]2[C:77]([CH3:78])=[C:76]([NH:79][C:80](=[O:88])[C:81]3[CH:86]=[CH:85][CH:84]=[CH:83][C:82]=3[Cl:87])[N:75]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:74]=2)=[O:72])[CH2:48][CH2:41]1

Participants

6

Reactant 5

HCID 1048PyrazoleHCID 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 68887576ethyl 5-amino-4-methyl-1-phenyl-1H-pyrazole-3-carboxylate

Product 1

HCID 597735984-Methyl-5-(2-chloro-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, 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-eb1d5f4ec47b4cddaf7ac4ad233e46bd
Source dataset
uspto-grants-2008_08
Patent number
US07417152B2

Reaction notes

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