5-Isocyanato-1,2,3-trimethoxybenzene → 1-[4-(9-chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)-cyclopent-2-enyl]3-(3,4,5-trimethoxy-phenyl)-urea

HRID 1838453ノート

反応式

HRID 1838453 の反応式
[NH2:1][CH:2]1[CH2:6][CH:5]([N:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[C:12]([Cl:17])[C:11]=3[C:10]3=[N:18][O:19][C:20]([CH3:21])=[C:9]3[C:8]2=[O:22])[CH:4]=[CH:3]1.[CH3:23][O:24][C:25]1[CH:26]=[C:27]([N:35]=[C:36]=[O:37])[CH:28]=[C:29]([O:33][CH3:34])[C:30]=1[O:31][CH3:32]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Cl:17][C:12]1[C:11]2[C:10]3[C:9](=[C:20]([CH3:21])[O:19][N:18]=3)[C:8](=[O:22])[N:7]([CH:5]3[CH2:6][CH:2]([NH:1][C:36]([NH:35][C:27]4[CH:26]=[C:25]([O:24][CH3:23])[C:30]([O:31][CH3:32])=[C:29]([O:33][CH3:34])[CH:28]=4)=[O:37])[CH:3]=[CH:4]3)[C:16]=2[CH:15]=[CH:14][CH:13]=1

参加物

5

反応物 2

HCID 5177665-Isocyanato-1,2,3-trimethoxybenzeneHCID 12094964HCID 12094964、化合物

生成物 1

HCID 103018101-[4-(9-chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)-cyclopent-2-enyl]3-(3,4,5-trimethoxy-phenyl)-urea収率 100.4%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a stirred solution of 5-(4amino-cyclopent-2-enyl)9-chloro-3-methyl-5H-isoxazolo[4,3-c]quinolin-4-one (69 mg, 0.22 mmol) in CH2Cl2 (5 mL) was added 3,4,5-trimethoxy-isocyanato benzene (55 mg, 0.26 mmol) and DMAP (catalytic amount) and stirred at rt. for 18 hours. The mixture was diluted with CH2Cl2, washed (brine), dried Na2SO4), filtered and concentrated. Column chromatography (silica gel, hexanes/ethyl acetate, gradient) gave the title compound (116 mg, 100%). Mass Spectrum (FIA) (m/z) 425.3 (M+1) 1H NMR (CDCl3): δ 7.45 (d, 1H); 7.40 (t, 1H); 7.33 (d, 1H); 6.58 (m, 3H); 5.95 (m, 1H); 5.83 (m, 1H); 5.18 (s, 1H); 3.78 (s, 9H); 2.98 (m, 2H); 2.05 (m, 2H).

後処理

  1. washwashed (brine), dried Na2SO4),
  2. filtrationfiltered
  3. concentrationconcentrated

出典と根拠

ORDレコード
ord-df7a22b50b754620a58738e72c881738
出典データセット
uspto-grants-2004_01
特許番号
US06673809B2

反応ノート

読み込み中…