3-Chloropropyl(diethyl)amine → HCID 24955985、化合物

HRID 607419ノート

反応式

HRID 607419 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH3:37])(=[O:36])=[N:9][C:10](=[O:35])[C:11]2[CH:16]=[C:15]([C:17]#[C:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([NH:25][C:26]([C:28]4[N:32]([CH3:33])[N:31]=[C:30]([CH3:34])[CH:29]=4)=[O:27])[CH:20]=3)[CH:14]=[N:13][CH:12]=2)=[CH:4][CH:3]=1.Cl[CH2:39][CH2:40][CH2:41][N:42]([CH2:45]C)[CH2:43]C>O1CCOCC1.CCOC(C)=O>[CH3:43][N:42]([CH3:45])[CH2:41][CH2:40][CH2:39][NH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH3:37])(=[O:36])=[N:9][C:10](=[O:35])[C:11]2[CH:16]=[C:15]([C:17]#[C:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([NH:25][C:26]([C:28]4[N:32]([CH3:33])[N:31]=[C:30]([CH3:34])[CH:29]=4)=[O:27])[CH:20]=3)[CH:14]=[N:13][CH:12]=2)=[CH:4][CH:3]=1

参加物

5

反応物 2

HCID 669183-Chloropropyl(diethyl)amineHCID 57657943HCID 57657943、化合物

生成物 1

HCID 24955985HCID 24955985、化合物収率 4%

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

N-[(4-{amino}phenyl)(methyl)oxido--sulfanylidene]-5-[(3-{[(1,3-dimethyl-1H-pyrazol-5-yl)carbonyl]amino}phenyl)ethynyl]nicotinamide (0.085 g, 0.168 mmol) was dissolved in dioxane (1.7 mL) then treated with (3-Chloro-propyl)-diethyl-amine (0.047 g, 0.252 mmol) and TEA (0.070 mL, 0.504 mmol). The reaction mixture was then heated to 100° C. for 48 h then cooled to room temperature. The cooled mixture was dissolved in EtOAc (5 mL) and then extracted with water (3×5 mL) and with brine (5 mL). The organic layer was dried over anhydrous Na2SO4(s), filtered and concentrated in vacuo. The crude mixture was purified via column chromatography (gradient eluant mixture of MeOH in EtOAc: 0% to 20% MeOH) to give the title compound (4 mg, 3.5%).

後処理

  1. temperaturethen cooled to room temperature
  2. extractionextracted with water (3×5 mL) and with brine (5 mL)
  3. dry with materialThe organic layer was dried over anhydrous Na2SO4(s)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude mixture was purified via column chromatography (gradient eluant mixture of MeOH in EtOAc: 0% to 20% MeOH)

出典と根拠

ORDレコード
ord-746de9b0bb2543a890fcb9cf0bc83b9c
出典データセット
uspto-grants-2011_03
特許番号
US07915443B2

反応ノート

読み込み中…