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

HRID 1694837ノート

反応式

HRID 1694837 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-3609dbcad2c2496c8ecbe3b5dd9ea86f
出典データセット
uspto-grants-2012_04
特許番号
US08158825B2

反応ノート

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