Phenethylamine → 3-chloro-4-methoxy-N-(2-{[(2-phenylethyl)amino]carbonyl}phenyl)benzamide

HRID 2099971ノート

反応式

HRID 2099971 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[C:5]([NH:7][C:8]1[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=O)=[O:6].[CH2:22]([NH2:30])[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(N(C(C)C)CC)(C)C.CCN=C=NCCCN(C)C.CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[C:5]([NH:7][C:8]1[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([NH:30][CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:12])=[O:6]

参加物

7

反応物 5

HCID 1001PhenethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 8914522-[(3-Chloro-4-methoxybenzoyl)amino]benzoic acid

生成物 1

HCID 115677123-chloro-4-methoxy-N-(2-{[(2-phenylethyl)amino]carbonyl}phenyl)benzamide収率 71.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of 42B (50 mg, 0.16 mmol) in DMF (5 mL) was treated with phenethylamine (150 μL, 1.6 mmol), diisopropylethylamine (42 mL, 0.32 mmol), and EDCI (31 mg, 0.32 mmol) at room temperature. After 2 hours Bop reagent (100 mg, 0.22 mmol) was added. After 30 minutes, the reaction was concentrated and purified by chromatography (SiO2, 30% EtOAc in hexanes) to afford 42C (47 mg, 70%). HPLC retention time: 2.79 minutes (YMC S-5 Combiscreen 4.6×50 mm, 10% to 90% MeOH/H2O w/0.2% H3PO4, 4 minute gradient).

後処理

  1. concentrationthe reaction was concentrated
  2. custompurified by chromatography (SiO2, 30% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-f8a99551315541f5ae4c60d2fcd1b146
出典データセット
uspto-grants-2009_08
特許番号
US07569725B2

反応ノート

読み込み中…