O-Phenylenediamine → HCID 16006048, compound

HRID 1694835Notes

Reaction equation

HRID 1694835 reaction equation
[NH:1]([C:8](=[O:28])[CH:9]([C:19]1[CH:27]=[CH:26][C:22]([C:23]([OH:25])=O)=[CH:21][N:20]=1)[C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN=C=NCCCN(C)C.[CH:40]1[CH:41]=[CH:42][C:43]2[N:48](O)N=[N:46][C:44]=2[CH:45]=1.C1(N)C=CC=CC=1N>CN(C=O)C>[NH2:46][C:44]1[CH:45]=[CH:40][CH:41]=[CH:42][C:43]=1[NH:48][C:23]([C:22]1[CH:26]=[CH:27][C:19]([CH:9]([C:8]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:28])[C:10]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:11])=[N:20][CH:21]=1)=[O:25]

Participants

6

Reactant 4

HCID 7243O-PhenylenediamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 59376457HCID 59376457, compound

Product 1

HCID 16006048HCID 16006048, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-[2-anilino-1-(anilinocarbonyl)-2-oxoethyl]nicotinic acid (35 mg, 0.093 mmol) in DMF (1 mL) at room temperature was added EDCI (22 mg, 0.11 mmol) and HOBT (14 mg, 0.10 mmol). The solution was stirred for 30 min and 1,2-phenylenediamine (34 mg, 0.31 mmol) was added in one portion. The reaction mixture was stirred at room temperature for 18 h and purified by reverse phase HPLC (5% to 80% MeCN in water) to give 2-(5-{[(2-aminophenyl)amino]carbonyl}pyridin-2-yl)-N,N′-diphenylmalonamide (16 mg, TFA salt, 21% from methyl 6-[2-anilino-1-(anilinocarbonyl)-2-oxoethyl]nicotinate) as a white solid: ESIMS calcd 466.2 (M++H), found 466.1 (M++H).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 18 h
  2. custompurified by reverse phase HPLC (5% to 80% MeCN in water)

Sources & evidence

ORD record
ord-a363bd758a294a7b946a3d1065fd3643
Source dataset
uspto-grants-2012_04
Patent number
US08158825B2

Reaction notes

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