O-Phenylenediamine → 2-(4-{[(2-aminophenyl)amino]carbonyl}phenyl)-2-hydroxy-N,N'-diphenylmalonamide

HRID 1694837Notes

Reaction equation

HRID 1694837 reaction equation
[NH:1]([C:8](=[O:29])[C:9]([C:20]1[CH:28]=[CH:27][C:23]([C:24]([OH:26])=O)=[CH:22][CH:21]=1)([C:11]([NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:12])[OH:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN=C=NCCCN(C)C.[CH:41]1[CH:42]=[CH:43][C:44]2[N:49](O)N=[N:47][C:45]=2[CH:46]=1.C1(N)C=CC=CC=1N>CN(C=O)C>[NH2:47][C:45]1[CH:46]=[CH:41][CH:42]=[CH:43][C:44]=1[NH:49][C:24]([C:23]1[CH:27]=[CH:28][C:20]([C:9]([OH:10])([C:8]([NH:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:29])[C:11]([NH:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[O:12])=[CH:21][CH:22]=1)=[O:26]

Participants

6

Reactant 4

HCID 7243O-PhenylenediamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 593764304-[2-Anilino-1-(anilinocarbonyl)-1-hydroxy-2-oxoethyl]benzoic acid

Product 1

HCID 444423562-(4-{[(2-aminophenyl)amino]carbonyl}phenyl)-2-hydroxy-N,N'-diphenylmalonamideYield 68.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-[2-anilino-1-(anilinocarbonyl)-1-hydroxy-2-oxoethyl]benzoic acid (31 mg, 0.079 mmol) in DMF (1.5 mL) at room temperature was added EDCI (18 mg, 0.094 mmol) and HOBT (13 mg, 0.096 mmol). The solution was stirred for 30 min and 1,2-phenylenediamine (31 mg, 0.29 mmol) was added in one portion. The reaction mixture was stirred at room temperature for 18 h and purified by reverse phase HPLC (30% to 95% MeCN in water) to give 2-(4-{[(2-aminophenyl)amino]carbonyl}phenyl)-2-hydroxy-N,N′-diphenylmalonamide (26 mg, TFA salt, 55%) as a white solid: 1H NMR (600 MHz, DMSO-d6) δ 10.10 (s br, 2H), 9.64 (s br, 1H), 7.97 (d, J=8.5 Hz, 2H), 7.82 (d, J=8.5 Hz, 2H), 7.70 (s, 1H), 7.69 (d, J=7.6 Hz, 2H), 7.32 (td, J=7.3, 2.1 Hz, 4H), 7.15 (d, J=7.3 Hz, 1H), 7.09 (t, J=6.4 Hz, 2H), 6.95 (td, J=8.2, 1.8 Hz, 1H), 6.76 (dd, J=7.9, 1.5 Hz, 1H), 6.58 (t, J=7.6 Hz, 1H), 4.89 (s br, 2H); ESIMS calcd 481.2 (M++H), found 481.1 (M++H).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 18 h
  2. custompurified by reverse phase HPLC (30% to 95% MeCN in water)

Sources & evidence

ORD record
ord-3609dbcad2c2496c8ecbe3b5dd9ea86f
Source dataset
uspto-grants-2012_04
Patent number
US08158825B2

Reaction notes

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