Benzenemethanamine, 4-chloro-3-(trifluoromethyl)- → 1-(4-Chloro-3-trifluoromethyl-benzyl)-3-(7-hydroxy-naphthalen-1-yl)-urea

HRID 351285

反応式

HRID 351285 の反応式
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][C:3]=1[C:10]([F:13])([F:12])[F:11].C1([O:20][C:21](=O)[NH:22][C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[C:30]([OH:33])[CH:31]=3)[CH:26]=[CH:25][CH:24]=2)C=CC=CC=1>CS(C)=O>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:7][C:21]([NH:22][C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[C:30]([OH:33])[CH:31]=3)[CH:26]=[CH:25][CH:24]=2)=[O:20])=[CH:4][C:3]=1[C:10]([F:11])([F:12])[F:13]

参加物

4

反応物 2

HCID 485440Benzenemethanamine, 4-chloro-3-(trifluoromethyl)-HCID 20090380(7-Hydroxy-naphthalen-1-yl)-carbamic acid phenyl ester

生成物 1

HCID 104757581-(4-Chloro-3-trifluoromethyl-benzyl)-3-(7-hydroxy-naphthalen-1-yl)-urea収率 77.1%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

4-Chloro-3-trifluoromethyl-benzylamine (150 mg, 0.71 mmol) and (7-hydroxy-naphthalen-1-yl)-carbamic acid phenyl ester (200 mg, 0.7 mmol) were combined and stirred at ambient temperature in DMSO (3 mL) overnight. The product was purified by directly injecting the crude reaction onto a reverse phase prep-HPLC (90–10% water:acetonitrile gradient). The appropriate fractions were lyophilized to yield 1-(4-Chloro-3-trifluoromethyl-benzyl)-3-(7-hydroxy-naphthalen-1-yl)-urea (212.7 mg, 0.54 mmol). MS (MH+) 394.9; 1H NMR (CD3OD) δ 4.41 (s, 2H), 7.09 (dd, 1H, J=2.4 Hz), 7.21–7.26 (m, 2H), 7.46 (d, 1H, J=7.3 Hz), 7.54 (d, 2H, J=1.0 Hz), 7.62 (d, 1H, J=8.2 Hz), 7.71–7.75 (m, 2H). HPLC Rt=4.4 min (90–10% water:acetonitrile gradient, 100% pure).

後処理

  1. customThe product was purified
  2. customreaction onto a reverse phase prep-HPLC (90–10% water:acetonitrile gradient)

出典と根拠

ORDレコード
ord-442e0fc0d0f647c7aef36c85fd0aa2d3
出典データセット
uspto-grants-2007_02
特許番号
US07183411B2

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