Triethylamine → 3-(1-isopropyl-6-(4-nitrophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-8-oxa-3-azabicyclo[3.2.1]octane

HRID 1093186ノート

反応式

HRID 1093186 の反応式
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=2)[N:5]=[C:4]2[N:17]([CH:20]([CH3:22])[CH3:21])[N:18]=[CH:19][C:3]=12.Cl.[CH:24]12[O:31][CH:28]([CH2:29][CH2:30]1)[CH2:27][NH:26][CH2:25]2.C(N(CC)CC)C>C(O)C>[CH:20]([N:17]1[C:4]2=[N:5][C:6]([C:8]3[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=3)=[N:7][C:2]([N:26]3[CH2:25][CH:24]4[O:31][CH:28]([CH2:29][CH2:30]4)[CH2:27]3)=[C:3]2[CH:19]=[N:18]1)([CH3:22])[CH3:21]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 219835368-Oxa-3-aza-bicyclo(3.2.1)octane hydrochlorideHCID 866293704-chloro-1-isopropyl-6-(4-nitrophenyl)-1H-pyrazolo[3,4-d]pyrimidine

生成物 1

HCID 665890533-(1-isopropyl-6-(4-nitrophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-8-oxa-3-azabicyclo[3.2.1]octane

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
140 °C

実験手順

A suspension of crude 4-chloro-1-isopropyl-6-(4-nitrophenyl)-1H-pyrazolo[3,4-d]pyrimidine (2.5 mmol maximum) and 8-oxa-3-aza-bicyclo[3.2.1]octane hydrochloride (0.47 g, 3.1 mmol) in ethanol (12 mL) was treated with triethylamine (1.1 mL) and then heated for 20 minutes in the microwave reactor at 140° C. At the completion of the reaction, the mixture was refrigerated overnight before collection of the precipitate via Buchner filtration. The solid was washed with methanol and dried under house vacuum to provide 3-(1-isopropyl-6-(4-nitrophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-8-oxa-3-azabicyclo[3.2.1]octane as a yellow powder (0.96 g, 97% over 2 steps). MS (ES+): 394.9, 396.0 (M+H)+

後処理

  1. customAt the completion of the reaction
  2. filtrationthe mixture was refrigerated overnight before collection of the precipitate via Buchner filtration
  3. washThe solid was washed with methanol
  4. customdried under house vacuum

出典と根拠

ORDレコード
ord-f47737fbb8174cb0ad7fcfb9bce70d42
出典データセット
uspto-grants-2012_03
特許番号
US08129371B2

反応ノート

読み込み中…