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Methylhydrazine → 6-(3-isopropyl-1-methyl-1H-pyrazol-5-yl)-4-methoxy-2-(3-methyl-1-tosyl-1H-indol-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

HRID 80803
ノート
印刷プレビュー

反応式

HRID 80803 の反応式
[CH3:1][O:2][C:3]1[C:4]2[CH2:32][N:31]([C:33](=O)[CH2:34][C:35](=O)[CH:36]([CH3:38])[CH3:37])[CH2:30][CH2:29][C:5]=2[N:6]=[C:7]([C:9]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:10]=2[C:11]([CH3:28])=[CH:12][N:13]3[S:18]([C:21]2[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=2)(=[O:20])=[O:19])[N:8]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=S)=CC=1.[CH3:63][NH:64][NH2:65]>C1COCC1.ClCCl.O>[CH:36]([C:35]1[CH:34]=[C:33]([N:31]2[CH2:30][CH2:29][C:5]3[N:6]=[C:7]([C:9]4[CH:17]=[CH:16][CH:15]=[C:14]5[C:10]=4[C:11]([CH3:28])=[CH:12][N:13]5[S:18]([C:21]4[CH:22]=[CH:23][C:24]([CH3:25])=[CH:26][CH:27]=4)(=[O:19])=[O:20])[N:8]=[C:3]([O:2][CH3:1])[C:4]=3[CH2:32]2)[N:64]([CH3:63])[N:65]=1)([CH3:37])[CH3:38]
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

7

反応物 3

HCID 6061MethylhydrazineHCID 87949Lawesson's reagentHCID 866902601-(4-methoxy-2-(3-methyl-1-tosyl-1H-indol-4-yl)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-4-methylpentane-1,3-dione

生成物 1

HCID 712405966-(3-isopropyl-1-methyl-1H-pyrazol-5-yl)-4-methoxy-2-(3-methyl-1-tosyl-1H-indol-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

試薬・触媒・溶媒 3

HCID 962
Water
溶媒
HCID 6344Dichloromethane溶媒
HCID 8028Tetrahydrofuran溶媒

反応条件

温度
120 °C

実験手順

To a solution of 1-(4-methoxy-2-(3-methyl-1-tosyl-1H-indol-4-yl)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-4-methylpentane-1,3-dione (350 mg, 0.624 mmol) in THF (3.3 mL), in a 2-5 mL microwave vial, was added Lawesson's reagent (278 mg, 0.687 mmol) and methyl hydrazine (0.049 mL, 0.94 mmol). The vessel was immediately sealed and heated via microwave irradiation at 120° C. for 10 minutes. The reaction was then cooled to room temperature and diluted with dichloromethane and water. The layers were separated and the aqueous layer was extracted two additional times with dichloromethane. The organic layers were combined, dried over Na2SO4, filtered, and concentrated. The resulting residue was purified via silica gel flash chromatography (45-67% ethyl acetate/heptanes) to provide 6-(3-isopropyl-1-methyl-1H-pyrazol-5-yl)-4-methoxy-2-(3-methyl-1-tosyl-1H-indol-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine. MS (ESI+) m/z 571.4 (M+H)+.

後処理

  1. customThe vessel was immediately sealed
  2. temperatureThe reaction was then cooled to room temperature
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted two additional times with dichloromethane
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue was purified via silica gel flash chromatography (45-67% ethyl acetate/heptanes)

出典と根拠

ORDレコード
ord-330158821a2f4cd4a7b5c34f6818b039
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08846656B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート