Pyrazole → 1-(pyridin-4-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 2114305Notes

Reaction equation

HRID 2114305 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][N:21]=[CH:20][CH: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].N(C1C=CN=CC=1)N.NC1N(C(OC(C)(C)C)=O)N=C(C(OC)=O)C=1.[N:61]1([C:70]2[CH:75]=[CH:74][N:73]=[CH:72][CH:71]=2)[CH2:66][CH2:65][CH:64]([CH2:67][CH2:68][NH2:69])[CH2:63][CH2:62]1>>[N:61]1([C:70]2[CH:75]=[CH:74][N:73]=[CH:72][CH:71]=2)[CH2:66][CH2:65][CH:64]([CH2:67][CH2:68][NH:69][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:19]=[CH:20][N:21]=[CH:22][CH:23]=3)[N:12]=2)=[O:10])[CH2:63][CH2:62]1

Participants

7

Reactant 6

HCID 1048PyrazoleHCID 220278212-[1-(Pyridin-4-yl)piperidin-4-yl]ethan-1-amineHCID 223202584-Hydrazinylpyridine hydrochlorideHCID 59223396Ethyl 3-cyano-3-methyl-2-oxopropanoateHCID 597733355-Amino-1-tert-butoxycarbonyl-3-methoxycarbonylpyrazoleHCID 69152953ethyl 5-amino-4-methyl-1-(pyridin-4-yl)-1H-pyrazole-3-carboxylate

Product 1

HCID 597733391-(pyridin-4-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-4-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. 4,6526,69) and 4-hydrazinopyridine hydrochloride (Apin Chemical, 25637 h)) 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-bd20270f0689464081b099627f76c76b
Source dataset
uspto-grants-2008_10
Patent number
US07432379B2

Reaction notes

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