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

HRID 2220763Notes

Reaction equation

HRID 2220763 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]([CH3:18])[N:12]=1)=O)C.[CH2:19](OC(=O)C(=O)C(C#N)C)[CH3:20].Cl.CNN.NC1N(C(OC(C)(C)C)=O)N=C(C(OC)=O)C=1.O=[C:52]1NC2C=CC=CC=2C(C2C=CC=CC=2)=N[CH:53]1[NH:69][C:70]([C:72]1[C:76]([CH3:77])=[C:75]([NH:78][C:79](=[O:87])[C:80]2[CH:85]=[CH:84][CH:83]=[CH:82][C:81]=2[Cl:86])[N:74]([C:88]2C=CC=CN=2)[N:73]=1)=[O:71]>>[N:12]1([C:11]2[CH:9]=[CH:18][N:13]=[CH:14][CH:15]=2)[CH2:20][CH2:19][CH:5]([CH2:52][CH2:53][NH:69][C:70]([C:72]2[C:76]([CH3:77])=[C:75]([NH:78][C:79](=[O:87])[C:80]3[CH:85]=[CH:84][CH:83]=[CH:82][C:81]=3[Cl:86])[N:74]([CH3:88])[N:73]=2)=[O:71])[CH2:4][CH2:3]1

Participants

7

Reactant 6

HCID 1048PyrazoleHCID 81793Methylhydrazine hydrochlorideHCID 22977830Ethyl 5-amino-1,4-dimethyl-1H-pyrazole-3-carboxylateHCID 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)amide

Product 1

HCID 597734264-Methyl-5-(2-chloro-benzoylamino)-1-methyl-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-dimethyl-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 methylhydrazine 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-3a002e4c2b584fb99d1816e2a8d7bfdf
Source dataset
uspto-grants-2008_08
Patent number
US07417152B2

Reaction notes

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