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

HRID 1694852노트

반응식

HRID 1694852 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-896baea7a58d4933b7d2e26823ec47ea
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08158825B2

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