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 2220761Notes

Reaction equation

HRID 2220761 reaction equation
N1C=CC=N1.C(OC(C1C(C)=C(N)N([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)N=1)=O)C.C(OC(=O)C(=O)C(C#N)C)C.Cl.Cl.N([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][N:40]=1)N.NC1N(C(OC(C)(C)C)=O)N=C(C(OC)=O)C=1.O=[C:63]1NC2C=CC=CC=2C(C2C=CC=CC=2)=N[CH:64]1[NH:80][C:81]([C:83]1[C:87]([CH3:88])=[C:86]([NH:89][C:90](=[O:98])[C:91]2[CH:96]=[CH:95][CH:94]=[CH:93][C:92]=2[Cl:97])[N:85]([C:99]2[CH:104]=[CH:103][CH:102]=[CH:101][N:100]=2)[N:84]=1)=[O:82]>>[N:40]1([C:22]2[CH:23]=[CH:18][N:19]=[CH:20][CH:21]=2)[CH2:41][CH2:42][CH:43]([CH2:63][CH2:64][NH:80][C:81]([C:83]2[C:87]([CH3:88])=[C:86]([NH:89][C:90](=[O:98])[C:91]3[CH:96]=[CH:95][CH:94]=[CH:93][C:92]=3[Cl:97])[N:85]([C:99]3[CH:104]=[CH:103][CH:102]=[CH:101][N:100]=3)[N:84]=2)=[O:82])[CH2:44][CH2:39]1

Participants

7

Reactant 6

HCID 1048PyrazoleHCID 64543982-Pyridone hydrazone dihydrochlorideHCID 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 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-da1ae0b6873a411083eee8bc988f168a
Source dataset
uspto-grants-2008_08
Patent number
US07417152B2

Reaction notes

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