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

HRID 2114307Notes

Reaction equation

HRID 2114307 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]=[CH:20][N:19]=2)[N:12]=1)=[O:10])C.C(OC(=O)[C:28](=[O:33])[CH:29]([C:31]#N)[CH3:30])C.[ClH:35].Cl.N(C1C=CC=CN=1)N.NC1N(C(OC(C)(C)C)=O)N=C(C(OC)=O)C=1.[N:62]1([C:71]2[CH:76]=[CH:75][N:74]=[CH:73][CH:72]=2)[CH2:67][CH2:66][CH:65]([CH2:68][CH2:69][NH2:70])[CH2:64][CH2:63]1>>[N:62]1([C:71]2[CH:76]=[CH:75][N:74]=[CH:73][CH:72]=2)[CH2:67][CH2:66][CH:65]([CH2:68][CH2:69][NH:70][C:9]([C:11]2[C:15]([CH3:16])=[C:14]([NH:17][C:28](=[O:33])[C:29]3[CH:31]=[CH:5][CH:4]=[CH:3][C:30]=3[Cl:35])[N:13]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)[N:12]=2)=[O:10])[CH2:64][CH2:63]1

Participants

7

Reactant 6

HCID 1048PyrazoleHCID 64543982-Pyridone hydrazone dihydrochlorideHCID 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 691518275-amino-4-methyl-1-pyridin-2-yl-1H-pyrazole-3-carboxylic acid ethyl ester

Product 1

HCID 597736051-(Pyridin-2-yl)-4-methyl-5-(2-chloro-benzoylamino)-1h-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-pyridin-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-hydrazinopyridine dihydrochloride (Aldrich, H1,710-4)) 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-28bbb84932e14e499dfb9dbd31daab36
Source dataset
uspto-grants-2008_10
Patent number
US07432379B2

Reaction notes

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