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

HRID 351285

반응식

HRID 351285 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-442e0fc0d0f647c7aef36c85fd0aa2d3
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07183411B2

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