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

HRID 2220765Notes

Reaction equation

HRID 2220765 reaction equation
N1C=[CH:4][CH:3]=N1.C(OC([C:11]1[C:15](C)=[C:14](N)[N:13]([C:18]2[CH:23]=[CH:22][C:21](F)=[CH:20]C=2)[N:12]=1)=O)C.C(OC(=O)C(=O)C(C#N)C)C.Cl.[F:37][C:38]1[CH:43]=[CH:42][C:41]([NH:44][NH2:45])=[CH:40][CH:39]=1.NC1N(C(OC(C)(C)C)=O)N=C(C(OC)=O)C=1.O=[C:64]1NC2C=CC=CC=2C(C2C=CC=CC=2)=N[CH:65]1[NH:81][C:82]([C:84]1[C:88]([CH3:89])=[C:87]([NH:90][C:91](=[O:99])[C:92]2[CH:97]=[CH:96][CH:95]=[CH:94][C:93]=2[Cl:98])N(C2C=CC=CN=2)N=1)=[O:83]>>[N:13]1([C:14]2[CH:15]=[CH:11][N:12]=[CH:4][CH:3]=2)[CH2:18][CH2:23][CH:22]([CH2:64][CH2:65][NH:81][C:82]([C:84]2[C:88]([CH3:89])=[C:87]([NH:90][C:91](=[O:99])[C:92]3[CH:97]=[CH:96][CH:95]=[CH:94][C:93]=3[Cl:98])[N:44]([C:41]3[CH:42]=[CH:43][C:38]([F:37])=[CH:39][CH:40]=3)[N:45]=2)=[O:83])[CH2:21][CH2:20]1

Participants

7

Reactant 6

HCID 1048PyrazoleHCID 699814-Fluorophenylhydrazine hydrochlorideHCID 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 69153527ethyl 5-amino-1-(4-fluorophenyl)-4-methyl-1H-pyrazole-3-carboxylate

Product 1

HCID 597735504-Methyl-5-(2-chloro-benzoylamino)-1-(p-fluorophenyl)-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-fluorophenyl)-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-fluorophenylhydrazine 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-c5983bd74d99466a87a4aa4901167794
Source dataset
uspto-grants-2008_08
Patent number
US07417152B2

Reaction notes

Loading…