5-(4-amino-cyclopent-2-enyl)-9-chloro-3-methyl-5H-isoxazolo[4,3-c]quinolin-4-one → N-[4(9-chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)-cyclopent-2-enyl]2-oxo-2-(3,4,5-trimethoxy-phenyl)-acetamide

HRID 1838452ノート

反応式

HRID 1838452 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.[O:23]=[C:24]([C:28]1[CH:33]=[C:32]([O:34][CH3:35])[C:31]([O:36][CH3:37])=[C:30]([O:38][CH3:39])[CH:29]=1)[C:25](Cl)=[O:26]>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:25](=[O:26])[C:24](=[O:23])[C:28]4[CH:29]=[C:30]([O:38][CH3:39])[C:31]([O:36][CH3:37])=[C:32]([O:34][CH3:35])[CH:33]=4)[CH:3]=[CH:4]3)[C:16]=2[CH:15]=[CH:14][CH:13]=1

参加物

5

反応物 2

HCID 120949645-(4-amino-cyclopent-2-enyl)-9-chloro-3-methyl-5H-isoxazolo[4,3-c]quinolin-4-oneHCID 226400793,4,5-Trimethoxyphenyl-2-oxoacetyl chloride

生成物 1

HCID 18753704N-[4(9-chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)-cyclopent-2-enyl]2-oxo-2-(3,4,5-trimethoxy-phenyl)-acetamide収率 38%

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-(4-amino-cyclopent-2-enyl)-9-chloro-3-methyl-5H-isoxazolo[4,3-c]quinolin-4-one (50 mg, 0.216 mmol) in CH2Cl2 (2 mL) was added oxo-(3,4,5-trimethoxy-phenyl)acetyl chloride (80 mg, 0.33 mmol, prepared from its acid and oxalyl chloride) and DMAP (catalytic amount) and stirred at r.t. 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 (33 mg, 38%). Mass Spectrum (FIA) (m/z) 538A 4 (A+1). 1H NMR (CDCl3): δ 7.80 (d, 1H); 7.50 (t, 1H); 7.35 (d, 1H); 6.00 (m, 2H); 5.40 (m, 1H); 5.21 (m, 111); 3.80-3.90 (m, 1H); 2.95 (s, 3H); 2.30 (m, 1H).

後処理

  1. washwashed (brine)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-f0f0ad6a9cd04a22aac3b19ca9340fa6
出典データセット
uspto-grants-2004_01
特許番号
US06673809B2

反応ノート

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