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

HRID 1067267ノート

反応式

HRID 1067267 の反応式
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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
177.5 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-aabf28c621164bda83c82eb82cb08a7f
出典データセット
uspto-grants-2001_06
特許番号
US06248753B1

反応ノート

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