N-Iodosuccinimide → N-cyclopentyl-8-iodo-7-phenylpyrazolo[1,5-a][1,3,5]triazin-4-amine

HRID 1296722ノート

反応式

HRID 1296722 の反応式
[CH:1]1([NH:6][C:7]2[N:12]3[N:13]=[C:14]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH:15]=[C:11]3[N:10]=[CH:9][N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[I:22]N1C(=O)CCC1=O>ClCCl>[CH:1]1([NH:6][C:7]2[N:12]3[N:13]=[C:14]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[C:15]([I:22])=[C:11]3[N:10]=[CH:9][N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

4

反応物 2

HCID 120273N-IodosuccinimideHCID 69447864N-cyclopentyl-7-phenylpyrazolo[1,5-a][1,3,5]triazin-4-amine

生成物 1

HCID 69447640N-cyclopentyl-8-iodo-7-phenylpyrazolo[1,5-a][1,3,5]triazin-4-amine収率 85%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

N-Cyclopentyl-7-phenylpyrazolo[1,5-a][1,3,5]triazin-4amine (0.25 g, 0.90 mmol) was dissolved in dichlorornethane. To this solution was added N-iodosuccinimide (300 mg, 1.33 mmol) and the resulting solution was stirred at room temperature for 30 minutes. Additional dichloromethane was added and the reaction mixture was extracted with 1N aqueous sodium hydroxide and with water. The organic phase was dried (magnesium sulfate), filtered and concentrated to give a solid. This solid was purified by silica gel chromatography (ethyl acetate:hexane 1:1) to give 310 mg (85%) of N-cyclopentyl-8-iodo-7-phenylpyrazolo[1,5-a][1,3,5]triazin-4-amine as a yellow solid. 1H-NMR (CDCl3): δ 8.35 (s, 1H), 7.98 (m, 2H), 7.55 (m, 3H), 6.64 (d, 1H), 4.60 (m, 1H), 2.3–2.1 (m, 2H), 2.0–1.6 (m, 6H); MS m/z 406 (M+1).

後処理

  1. extractionthe reaction mixture was extracted with 1N aqueous sodium hydroxide and with water
  2. dry with materialThe organic phase was dried (magnesium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a solid
  6. customThis solid was purified by silica gel chromatography (ethyl acetate:hexane 1:1)

出典と根拠

ORDレコード
ord-a99ba0b9b9694940bdfd17c5c2a1455f
出典データセット
uspto-grants-2007_07
特許番号
US07247626B2

反応ノート

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