Dimethylamine → 7-(2-Dimethylamino-ethoxy)-4-(3-hydroxy-4-methyl-phenylamino)-6-methoxy-quinoline-3-carbonitrile

HRID 1934956ノート

反応式

HRID 1934956 の反応式
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[C:20]([OH:25])[CH:19]=3)=[C:10]([C:15]#[N:16])[CH:11]=[N:12]2)=[CH:7][C:6]=1[O:26][CH3:27].[I-].[Na+].[CH3:30][NH:31][CH3:32]>O1CCCC1>[CH3:30][N:31]([CH3:32])[CH2:2][CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[C:20]([OH:25])[CH:19]=3)=[C:10]([C:15]#[N:16])[CH:11]=[N:12]2)=[CH:7][C:6]=1[O:26][CH3:27]

参加物

5

反応物 3

HCID 674DimethylamineHCID 5238Sodium IodideHCID 224666497-(2-Chloro-ethoxy)-4-(3-hydroxy-4-methyl-phenylamino)-6-methoxy-quinoline-3-carbonitrile

生成物 1

HCID 102718227-(2-Dimethylamino-ethoxy)-4-(3-hydroxy-4-methyl-phenylamino)-6-methoxy-quinoline-3-carbonitrile

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
125 °C

実験手順

A mixture of 1 g (2.38 mmol) of 7-(2-chloro-ethoxy)-4-(3-hydroxy-4-methyl-phenylamino)-6-methoxy-quinoline-3-carbonitrile and 0.078 g of sodium iodide in 19.5 ml of 2M dimethylamine in tetrahydrofuran was placed in a sealed tube and heated to 125° C. for 14 hr. The solvent was removed and the residue was mixed with warm ethyl acetate and saturated sodium bicarbonate solution. The organic layer was separated and dried over magnesium sulfate. Solvent was removed and the residue was chromatographed on silica gel eluting with ethyl acetate-methanol-triethylamine 70:30:2.5 giving 0.89 g of the title compound as a light yellow solid: mass spectrum (electrospray, m/e) M+H 393.0; (M+2H)+2 196.9.

後処理

  1. customwas placed in a sealed tube
  2. customThe solvent was removed
  3. additionthe residue was mixed with warm ethyl acetate and saturated sodium bicarbonate solution
  4. customThe organic layer was separated
  5. dry with materialdried over magnesium sulfate
  6. customSolvent was removed
  7. customthe residue was chromatographed on silica gel eluting with ethyl acetate-methanol-triethylamine 70:30:2.5 giving 0.89 g of the title compound as a light yellow solid

出典と根拠

ORDレコード
ord-1ef31e3dcf924b53a22e0c98c3cc20cc
出典データセット
uspto-grants-2002_05
特許番号
US06384051B1

反応ノート

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