Chloroform → 2-(Chloromethyl)(1,3)oxazolo(4,5-b)pyridine

HRID 1828297

反応式

HRID 1828297 の反応式
[NH2:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.O.[C:10]1([CH3:20])C=CC(S(O)(=O)=O)=CC=1.C(Cl)(Cl)[Cl:22]>COCCOCCOC.C(O)C>[Cl:22][CH2:10][C:20]1[O:8][C:7]2[C:2]([N:1]=1)=[N:3][CH:4]=[CH:5][CH:6]=2

参加物

6

反応物 3

HCID 6212ChloroformHCID 281142-Amino-3-HydroxypyridineHCID 521998p-Toluenesulfonic acid monohydrate

生成物 1

HCID 27645692-(Chloromethyl)(1,3)oxazolo(4,5-b)pyridine

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8150Diglyme溶媒

反応条件

温度
80 °C

実験手順

2-Amino-3-pyridinol (1.1 g, Chemical Abstracts #16867-03-1) and chloromethyltrimethylorthoformate (2.27 g) were combined in diglyme (in 21 mL) and heated at 80° C. for 6 hours. The mixture was treated with p-toluenesulfonic acid hydrate (4 mg) and heated at 80° C. for an additional 48 hours. The mixture was allowed to cool to room temperature and diluted with chloroform (40 mL) and ethanol (10 mL). The mixture was filtered and the filtrate concentrated under reduced pressure. The residue was dissolved in methanol and filtered again. The resulting filtrate was concentrated under reduced pressure to provide the title compound and then dissolved in acetonitrile (35 mL) and used as a solution in the next step. 1H NMR (CDCl3, 300 MHz) δ 4.82 (2H, s), 7.38 (dd, 1H, J=8.7, 5.4 Hz), 7.89 (dd, 1H, J=8.7, 1.5 Hz), 8.62 (dd, 1H, J=5.4, 1.5 Hz). MS (DCI/NH3) m/z 169 (M+H)+.

後処理

  1. temperatureheated at 80° C. for an additional 48 hours
  2. temperatureto cool to room temperature
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate concentrated under reduced pressure
  5. dissolutionThe residue was dissolved in methanol
  6. filtrationfiltered again
  7. concentrationThe resulting filtrate was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-8bd8cbf86d2a4cff85f86197521bcdca
出典データセット
uspto-grants-2006_06
特許番号
US07057042B2

関連ノート

読み込み中…