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 2114314Notes

Reaction equation

HRID 2114314 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]([CH3:18])[N:12]=1)=[O:10])C.C(OC(=O)[C:23](=[O:28])[CH:24]([C:26]#N)[CH3:25])C.[ClH:30].CNN.NC1N(C(OC(C)(C)C)=O)N=C(C(OC)=O)C=1.[N:51]1([C:60]2[CH:65]=[CH:64][N:63]=[CH:62][CH:61]=2)[CH2:56][CH2:55][CH:54]([CH2:57][CH2:58][NH2:59])[CH2:53][CH2:52]1>>[N:51]1([C:60]2[CH:65]=[CH:64][N:63]=[CH:62][CH:61]=2)[CH2:56][CH2:55][CH:54]([CH2:57][CH2:58][NH:59][C:9]([C:11]2[C:15]([CH3:16])=[C:14]([NH:17][C:23](=[O:28])[C:24]3[CH:26]=[CH:5][CH:4]=[CH:3][C:25]=3[Cl:30])[N:13]([CH3:18])[N:12]=2)=[O:10])[CH2:53][CH2:52]1

Participants

7

Reactant 6

HCID 1048PyrazoleHCID 81793Methylhydrazine hydrochlorideHCID 220278212-[1-(Pyridin-4-yl)piperidin-4-yl]ethan-1-amineHCID 22977830Ethyl 5-amino-1,4-dimethyl-1H-pyrazole-3-carboxylateHCID 59223396Ethyl 3-cyano-3-methyl-2-oxopropanoateHCID 597733355-Amino-1-tert-butoxycarbonyl-3-methoxycarbonylpyrazole

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. 4,6526,69) 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-1a9b9c90b7e0442bb10cf2dc6a66d1d8
Source dataset
uspto-grants-2008_10
Patent number
US07432379B2

Reaction notes

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