Iodine → HCID 57444149、化合物

HRID 44627

反応式

HRID 44627 の反応式
N[C:2]1[N:11]=[CH:10][C:9]2[CH2:8][CH2:7][C:6]3[C:12]([C:16]([NH:18][C@@H:19]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH2:20][N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)=[O:17])=[N:13][N:14]([CH3:15])[C:5]=3[C:4]=2[N:3]=1.[I-:33].[Cs+].II.N(OCCC(C)C)=O>C(COC)OC.[Cu](I)I>[I:33][C:2]1[N:11]=[CH:10][C:9]2[CH2:8][CH2:7][C:6]3[C:12]([C:16]([NH:18][C@@H:19]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH2:20][N:21]4[CH2:22][CH2:23][O:24][CH2:25][CH2:26]4)=[O:17])=[N:13][N:14]([CH3:15])[C:5]=3[C:4]=2[N:3]=1

参加物

7

反応物 4

HCID 807IodineHCID 8053Isoamyl NitriteHCID 24601Cesium iodideHCID 574441508-amino-1-methyl-N-[(1S)-2-morpholin-4-yl-1-phenylethyl]-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide

生成物 1

HCID 57444149HCID 57444149、化合物収率 40%

試薬・触媒・溶媒 2

HCID 83717Copper iodide触媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

To a well stirred and warm suspension of 8-amino-1-methyl-N-[(1S)-2-morpholin-4-yl-1-phenylethyl]-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide (3 g, 6.92 mmol) in dimethoxyethane (240 mL), maintained in an inert atmosphere of argon, cesium iodide (2.16 g, 8.3 mmol), bisublimated iodine (870 mg, 3.46 mmol), copper iodide (460 mg, 2.42 mmol) and isopentyl nitrite (1.71 mL, 1.5 g, 12.46 mmol) were added, in sequence. The reaction mixture was stirred vigorously at 65-70° C. for 18 hours. After cooling in an ice-water bath, the solid was filtered off and the filtrate was diluted with dichloromethane (100 mL), washed with 30% ammonium hydroxide (50 mL), sodium thiosulphate (100 mL), brine and dried over anhydrous Na2SO4. The crude was purified by flash chromatography on silica gel (eluant: dichloromethane/methanol 95:59) and 1.48 g of the title compound was isolated (40% yield).

後処理

  1. temperaturewarm
  2. additionwere added, in sequence
  3. stirringThe reaction mixture was stirred vigorously at 65-70° C. for 18 hours
  4. temperatureAfter cooling in an ice-water bath
  5. filtrationthe solid was filtered off
  6. additionthe filtrate was diluted with dichloromethane (100 mL)
  7. washwashed with 30% ammonium hydroxide (50 mL), sodium thiosulphate (100 mL), brine
  8. dry with materialdried over anhydrous Na2SO4
  9. customThe crude was purified by flash chromatography on silica gel (eluant: dichloromethane/methanol 95:59)

出典と根拠

ORDレコード
ord-b27aceb55e484bbc8f9a5441de48ba65
出典データセット
uspto-grants-2013_09
特許番号
US08541429B2

関連ノート

読み込み中…