Pyrazole → 4-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)amide

HRID 2220757Notes

Reaction equation

HRID 2220757 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][CH:21]=[CH:20][N: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].Cl.N(C1C=CC=CN=1)N.NC1N(C(OC(C)(C)C)=O)N=C(C(OC)=O)C=1.[NH2:62][CH:63]1[C:69](=[O:70])[NH:68][C:67]2[CH:71]=[CH:72][CH:73]=[CH:74][C:66]=2[C:65]([C:75]2[CH:80]=[CH:79][CH:78]=[CH:77][CH:76]=2)=[N:64]1>>[O:70]=[C:69]1[NH:68][C:67]2[CH:71]=[CH:72][CH:73]=[CH:74][C:66]=2[C:65]([C:75]2[CH:76]=[CH:77][CH:78]=[CH:79][CH:80]=2)=[N:64][CH:63]1[NH:62][C:9]([C:11]1[C:15]([CH3:16])=[C:14]([NH:17][C:28](=[O:33])[C:29]2[CH:31]=[CH:5][CH:4]=[CH:3][C:30]=2[Cl:35])[N:13]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[N:12]=1)=[O:10]

Participants

7

Reactant 6

HCID 1048PyrazoleHCID 42596493-Amino-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-oneHCID 64543982-Pyridone hydrazone dihydrochlorideHCID 59223396Ethyl 3-cyano-3-methyl-2-oxopropanoateHCID 597733355-Amino-1-tert-butoxycarbonyl-3-methoxycarbonylpyrazoleHCID 691518275-amino-4-methyl-1-pyridin-2-yl-1H-pyrazole-3-carboxylic acid ethyl ester

Product 1

HCID 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)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 3-amino-5-phenyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one (prepared as described in Procedure 20) using the method of Procedure 10.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-edec56cfb01d4b87a1b245b57887e5c0
Source dataset
uspto-grants-2008_08
Patent number
US07417152B2

Reaction notes

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