O-Phenylenediamine → HCID 11988294, compound

HRID 1694828Notes

Reaction equation

HRID 1694828 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:30])[CH:10]([C:21]2[CH:29]=[CH:28][C:24]([C:25]([OH:27])=O)=[CH:23][CH:22]=2)[C:11]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=2)=[O:12])[CH:5]=[CH:6][CH:7]=1.CCN=C=NCCCN(C)C.[CH:42]1[CH:43]=[CH:44][C:45]2[N:50](O)N=[N:48][C:46]=2[CH:47]=1.C1(N)C=CC=CC=1N>CN(C=O)C>[NH2:48][C:46]1[CH:47]=[CH:42][CH:43]=[CH:44][C:45]=1[NH:50][C:25]([C:24]1[CH:23]=[CH:22][C:21]([CH:10]([C:11]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=2)=[O:12])[C:9]([NH:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)=[O:30])=[CH:29][CH:28]=1)=[O:27]

Participants

6

Reactant 4

HCID 7243O-PhenylenediamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 59376460HCID 59376460, compound

Product 1

HCID 11988294HCID 11988294, compoundYield 61.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(2-[(3-chlorophenyl)amino]-1-{[(3-chlorophenyl)amino]carbonyl}-2-oxoethyl)benzoic acid (61 mg, 0.14 mmol) in DMF (3 mL) at room temperature was added EDCI (31 mg, 0.16 mmol) and HOBT (22 mg, 0.16 mmol). The solution was stirred for 30 min and 1,2-phenylenediamine (45 mg, 0.42 mmol) was added in one portion. The reaction mixture was stirred at room temperature for 18 h and purified directly by reverse phase HPLC (20% to 80% MeCN in water) to give 2-(4-{[(2-aminophenyl)amino]carbonyl}phenyl)-N,N′-bis(3-chlorophenyl)malonamide (46 mg, TFA salt, 52%) as a white solid: 1H NMR (600 MHz, CD3OD) δ 8.06 (d, J=8.2 Hz, 2H), 7.79 (t, J=2.1 Hz, 2H), 7.70 (d, J=8.2 Hz, 2H), 7.44 (dd, J=8.2, 1.2 Hz, 2H), 7.36 (d, J=7.9 Hz, 1H), 7.33-7.24 (m, 5H), 7.11 (dd, J=7.9, 0.8 Hz, 2H); ESIMS calcd 533.1 (M++H), found 533.0 (M++H).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 18 h
  2. custompurified directly by reverse phase HPLC (20% to 80% MeCN in water)

Sources & evidence

ORD record
ord-9f914006865546508c80ff319e0554bc
Source dataset
uspto-grants-2012_04
Patent number
US08158825B2

Reaction notes

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