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

HRID 1296722노트

반응식

HRID 1296722 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-a99ba0b9b9694940bdfd17c5c2a1455f
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07247626B2

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