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

HRID 1768367

반응식

HRID 1768367 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8150Diglyme용매

반응 조건

온도
80 °C

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-46bd4969c17b4c21b8a4dc962aaadb7b
출처 데이터셋
uspto-grants-2007_06
특허 번호
US07235661B2

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