Butylethylamine → Butyl-[3,6dimethyl-1-(2,4,6-trimethylphenyl)-1H-pyrazolo[3,4-b]pyridin-4-yl]ethylamine

HRID 1067267노트

반응식

HRID 1067267 반응식
Cl[C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]2[N:9]([C:13]3[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=3[CH3:21])[N:10]=[C:11]([CH3:12])[C:3]=12.[CH2:22]([NH:26][CH2:27][CH3:28])[CH2:23][CH2:24][CH3:25]>CS(C)=O>[CH2:22]([NH:26][CH2:27][CH2:28][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]2[N:9]([C:13]3[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=3[CH3:21])[N:10]=[C:11]([CH3:12])[C:3]=12)[CH2:23][CH2:24][CH3:25]

참가 물질

4

반응물 2

HCID 25914ButylethylamineHCID 211929064-chloro-3,6-dimethyl-1-(2,4,6-trimethylphenyl)-1H-pyrazolo[3,4-b]pyridine

생성물 1

HCID 53744748Butyl-[3,6dimethyl-1-(2,4,6-trimethylphenyl)-1H-pyrazolo[3,4-b]pyridin-4-yl]ethylamine

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
177.5 °C

실험 절차

A mixture of 4-chloro-3,6-dimethyl-1-(2,4,6-trimethylphenyl)-1H-pyrazolo[3,4-b]pyridine (98 mg, 0.33 mmol), N-butylethylamine (1 ml) in DMSO (2 ml) was heated in an oil bath at 175-180° C. for 20 hours. The reaction mixture was quenched with saturated ammonium chloride and extracted with EtOAc. The organic layer was washed with brine, dried, and concentrated to give a brown oil. The oil residue was purified through silica gel column chromatography using EtOAc/Hexane in a ratio of 1/9 as eluent to give a colorless oil. 1H NMR (CDCl3) 6.92 (s, 2H), 6.29 (s, 1H), 3.42 (q, 2H), 3.27 (t, 2H), 2.65 (s, 3H), 2.44 (s, 3H), 2.30 (s, 3H), 1.91 (s, 6H), 1.57 (m, 2H), 1.33 (m, 2H), 1.13 (t, 3H), 0.90 (t, 3H) ppm. IR (neat) 2960, 2920, 1570 cm−1. High MS, calc. 364.2627, found 364.26306.

후처리

  1. customThe reaction mixture was quenched with saturated ammonium chloride
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customto give a brown oil
  7. customThe oil residue was purified through silica gel column chromatography
  8. customto give a colorless oil

출처 및 근거

ORD 기록
ord-aabf28c621164bda83c82eb82cb08a7f
출처 데이터셋
uspto-grants-2001_06
특허 번호
US06248753B1

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