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

HRID 2220758Notes

Reaction equation

HRID 2220758 reaction equation
N1C=[CH:4][CH:3]=N1.C(O[C:9]([C:11]1[C:15](C)=[C:14](N)[N:13]([C:18]2[CH:23]=[C:22](C)[N:21]=[C:20]([CH3:25])N=2)N=1)=O)C.C(OC(=O)C(=O)C(C#N)C)C.[NH:37]([C:39]1[CH:44]=[C:43]([CH3:45])[N:42]=[C:41]([CH3:46])[N:40]=1)[NH2:38].NC1N(C(OC(C)(C)C)=O)N=C(C(OC)=O)C=1.O=C1NC2C=CC=CC=2C(C2C=CC=CC=2)=N[CH:66]1[NH:82][C:83]([C:85]1[C:89]([CH3:90])=[C:88]([NH:91][C:92](=[O:100])[C:93]2[CH:98]=[CH:97][CH:96]=[CH:95][C:94]=2[Cl:99])N(C2C=CC=CN=2)N=1)=[O:84]>>[N:13]1([C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:25]=2)[CH2:14][CH2:15][CH:11]([CH2:9][CH2:66][NH:82][C:83]([C:85]2[C:89]([CH3:90])=[C:88]([NH:91][C:92](=[O:100])[C:93]3[CH:98]=[CH:97][CH:96]=[CH:95][C:94]=3[Cl:99])[N:37]([C:39]3[CH:44]=[C:43]([CH3:45])[N:42]=[C:41]([CH3:46])[N:40]=3)[N:38]=2)=[O:84])[CH2:4][CH2:3]1

Participants

7

Reactant 6

HCID 1048PyrazoleHCID 7363954-Hydrazinyl-2,6-dimethylpyrimidineHCID 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 691527945-amino-1-(2,6-dimethylpyrimidin-4-yl)-4-methyl-1H-pyrazole-3-carboxylic acid ethyl ester

Product 1

HCID 597735744-Methyl-5-(2-chlorobenzoylamino)-1-(2,6-dimethylpyrimidin-4-yl)-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-(2,6-dimethylpyrimidin-4-yl)-4-methyl-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 4-hydrazino-2,6-dimethylpyrimidine (Ryan Scientific, BTB 10371)) 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-542aeef379bd4da093c6a51a5ef2f67a
Source dataset
uspto-grants-2008_08
Patent number
US07417152B2

Reaction notes

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