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

HRID 2220759Notes

Reaction equation

HRID 2220759 reaction equation
N1[CH:5]=[CH:4][CH:3]=N1.C(O[C:9]([C:11]1[C:15](C)=[C:14](N)[N:13]([C:18]2N=CC=CN=2)[N:12]=1)=O)C.[CH2:24](OC(=O)C(=O)C(C#N)C)[CH3:25].[NH:35]1[CH:40]=[CH:39][CH:38]=[N:37][C:36]1=O.NC1N(C(OC(C)(C)C)=O)N=C(C(OC)=O)C=1.O=[C:60]1NC2C=CC=CC=2C(C2C=CC=CC=2)=N[CH:61]1[NH:77][C:78]([C:80]1[C:84]([CH3:85])=[C:83]([NH:86][C:87](=[O:95])[C:88]2[CH:93]=[CH:92][CH:91]=[CH:90][C:89]=2[Cl:94])[N:82](C2C=CC=CN=2)[N:81]=1)=[O:79]>>[N:12]1([C:11]2[CH:9]=[CH:18][N:13]=[CH:14][CH:15]=2)[CH2:25][CH2:24][CH:5]([CH2:60][CH2:61][NH:77][C:78]([C:80]2[C:84]([CH3:85])=[C:83]([NH:86][C:87](=[O:95])[C:88]3[CH:93]=[CH:92][CH:91]=[CH:90][C:89]=3[Cl:94])[N:82]([C:36]3[N:37]=[CH:38][CH:39]=[CH:40][N:35]=3)[N:81]=2)=[O:79])[CH2:4][CH2:3]1

Participants

7

Reactant 6

HCID 1048PyrazoleHCID 684012(1H)-PyrimidinoneHCID 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 69153554ethyl 5-amino-4-methyl-1-(pyrimidin-2-yl)-1H-pyrazole-3-carboxylate

Product 1

HCID 597735514-Methyl-5-(2-chlorobenzoylamino)-1-(pyrimidin-2-yl)-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-pyrimidin-2-yl-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 2(1H)-pyrimidinone, hydrazone (Ambinter, PFR-114431)) 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-b4280b14bb504268a2b9b1c8e930ba3c
Source dataset
uspto-grants-2008_08
Patent number
US07417152B2

Reaction notes

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