2-Amino-4-phenylphenol → 2-(4-{[(4-hydroxybiphenyl-3-yl)amino]carbonyl}phenyl)-N,N'-diphenylmalonamide

HRID 1694852

Reaction equation

HRID 1694852 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][CH: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.C1C=CC2N(O)N=NC=2C=1.[NH2:50][C:51]1[CH:56]=[C:55]([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)[CH:54]=[CH:53][C:52]=1[OH:63]>CN(C=O)C>[OH:63][C:52]1[CH:53]=[CH:54][C:55]([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)=[CH:56][C:51]=1[NH:50][C:23]([C:22]1[CH:21]=[CH:20][C:19]([CH:9]([C:10]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:11])[C:8]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:28])=[CH:27][CH:26]=1)=[O:25]

Participants

6

Reactant 4

HCID 145622-Amino-4-phenylphenolHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 593764614-[2-Anilino-1-(anilinocarbonyl)-2-oxoethyl]benzoic acid

Product 1

HCID 160063532-(4-{[(4-hydroxybiphenyl-3-yl)amino]carbonyl}phenyl)-N,N'-diphenylmalonamideYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-[2-anilino-1-(anilinocarbonyl)-2-oxoethyl]benzoic acid (33 mg, 0.088 mmol) in DMF (1 mL) at room temperature was added EDCI (13 mg, 0.094 mmol) and HOBT (19 mg, 0.14 mmol). The solution was stirred for 30 min and 2-amino-4-phenylphenol (33 mg, 0.18 mmol) was added in one portion. The reaction mixture was stirred at room temperature for 18 h and purified directly by reverse phase HPLC (40% to 95% MeCN in water) to give 2-(4-{[(4-hydroxybiphenyl-3-yl)amino]carbonyl}phenyl)-N,N′-diphenylmalonamide (27 mg, 57%) as a white solid: 1H NMR (600 MHz, DMSO-d6) δ 10.27 (s br, 2H), 9.96 (s br, 1H), 9:58 (s br, 1H), 8.01-7.97 (m, 3H), 7.59-7.55 (m, 8H), 7.41 (t, J=7.9 Hz, 2H), 7.35-7.27 (m, 6H), 7.04 (t, J=7.0 Hz, 2H), 6.98 (d, J=8.2 Hz, 1H), 4.97 (s, 1H); ESIMS calcd 542.2 (M++H), found 542.1 (M++H).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 18 h
  2. custompurified directly by reverse phase HPLC (40% to 95% MeCN in water)

Sources & evidence

ORD record
ord-896baea7a58d4933b7d2e26823ec47ea
Source dataset
uspto-grants-2012_04
Patent number
US08158825B2

Linked notes

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