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(Dimethyl-1,3-thiazol-5-yl)methanamine → 7-(3,5-dimethyl-4-isoxazolyl)-N-[(2,4-dimethyl-1,3-thiazol-5-yl)methyl]-6-(methyloxy)-3-nitro-4-quinolinamine

HRID 1043003
ノート
印刷プレビュー

反応式

HRID 1043003 の反応式
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:14]3[C:15]([CH3:20])=[N:16][O:17][C:18]=3[CH3:19])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[N+:21]([O-:23])=[O:22].[CH3:24][C:25]1[S:26][C:27]([CH2:31][NH2:32])=[C:28]([CH3:30])[N:29]=1>C(#N)C.O>[CH3:20][C:15]1[C:14]([C:8]2[CH:7]=[C:6]3[C:11]([C:2]([NH:32][CH2:31][C:27]4[S:26][C:25]([CH3:24])=[N:29][C:28]=4[CH3:30])=[C:3]([N+:21]([O-:23])=[O:22])[CH:4]=[N:5]3)=[CH:10][C:9]=2[O:12][CH3:13])=[C:18]([CH3:19])[O:17][N:16]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 25219195(Dimethyl-1,3-thiazol-5-yl)methanamineHCID 574655804-(4-Chloro-6-methoxy-3-nitroquinolin-7-yl)-3,5-dimethylisoxazole2 回

生成物 1

HCID 672080477-(3,5-dimethyl-4-isoxazolyl)-N-[(2,4-dimethyl-1,3-thiazol-5-yl)methyl]-6-(methyloxy)-3-nitro-4-quinolinamine

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

反応条件

温度
80 °C

実験手順

To a solution of 4-chloro-7-(3,5-dimethyl-4-isoxazolyl)-6-(methyloxy)-3-nitroquinoline (for a preparation see Intermediate 18, 1.5 g) in acetonitrile was added [(2,4-dimethyl-1,3-thiazol-5-yl)methyl]amine (1.6 g) and the resulting mixture was stirred overnight at 80° C. Another portion of amine (0.64 g) was added and the mixture was stirred at 80° C. for 6 h. The reaction mixture was diluted with water, extracted with DCM and the organic phase were dried over Na2SO4, and concentrated to dryness to give a dark red oil. The residue was purified by flash chromatography on silica gel, eluting with DCM/methanol (99:1 then 95:5) to give 7-(3,5-dimethyl-4-isoxazolyl)-N-[(2,4-dimethyl-1,3-thiazol-5-yl)methyl]-6-(methyloxy)-3-nitro-4-quinolinamine (1.13 g) as an orange oil.

後処理

  1. stirringthe mixture was stirred at 80° C. for 6 h
  2. extractionextracted with DCM
  3. dry with materialthe organic phase were dried over Na2SO4
  4. concentrationconcentrated to dryness
  5. customto give a dark red oil
  6. customThe residue was purified by flash chromatography on silica gel
  7. washeluting with DCM/methanol (99:1

出典と根拠

ORDレコード
ord-78fed5b6334b4d09a77e76328fbff820
出典データセット
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08557984B2

反応ノート

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