Potassium Carbonate → N-sec-butyl-5-(4-(2-fluorophenyl)oxazol-5-yl)thiazolo[5,4-b]pyridin-2-amine

HRID 1452980노트

반응식

HRID 1452980 반응식
[CH:1]([NH:5][C:6]1[S:7][C:8]2[C:13]([N:14]=1)=[CH:12][CH:11]=[C:10]([CH:15]=[O:16])[N:9]=2)([CH2:3][CH3:4])[CH3:2].[F:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH:24]([N+:35]#[C-:36])S(C1C=CC(C)=CC=1)(=O)=O.C([O-])([O-])=O.[K+].[K+]>CCO>[CH:1]([NH:5][C:6]1[S:7][C:8]2[C:13]([N:14]=1)=[CH:12][CH:11]=[C:10]([C:15]1[O:16][CH:36]=[N:35][C:24]=1[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[F:17])[N:9]=2)([CH2:3][CH3:4])[CH3:2]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 467382311-Fluoro-2-(isocyano(tosyl)methyl)benzeneHCID 575272422-(Sec-butylamino)thiazolo[5,4-b]pyridine-5-carbaldehyde

생성물 1

HCID 15987489N-sec-butyl-5-(4-(2-fluorophenyl)oxazol-5-yl)thiazolo[5,4-b]pyridin-2-amine수율 30%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A solution of 2-(sec-butylamino)thiazolo[5,4-b]pyridine-5-carbaldehyde (presumed 0.24 mmol, 1.0 eq.), 1-fluoro-2-(isocyano(tosyl)methyl)benzene (0.0874 g, 0.302 mmol, 1.3 eq.), and K2CO3 (0.0654 g, 0.473 mmol, 2.0 eq.) in EtOH (2.4 mL) was refluxed overnight. After cooling to room temperature, the reaction mixture was concentrated in vacuo, and the residue was taken up in EtOAc and water. After separation of the layers, the organic layer was washed with saturated aqueous NaHCO3 and brine, dried over Na2SO4, filtered, and concentrated in vacuo. MeOH was added to the residue, and the mixture was subjected to autoprep. The appropriate fractions were collected, and NaHCO3 (s) was added. The solution was then concentrated in vacuo not to dryness and extracted with EtOAc (3×). The organic layers were combined, dried over Na2SO4, filtered, and concentrated in vacuo to give N-sec-butyl-5-(4-(2-fluorophenyl)oxazol-5-yl)thiazolo[5,4-b]pyridin-2-amine as a yellow solid (0.0264 g, 30% yield). LC/MS (MH)=369.20.

후처리

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customAfter separation of the layers
  3. washthe organic layer was washed with saturated aqueous NaHCO3 and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. additionMeOH was added to the residue
  8. customThe appropriate fractions were collected
  9. additionNaHCO3 (s) was added
  10. concentrationThe solution was then concentrated in vacuo not to dryness
  11. extractionextracted with EtOAc (3×)
  12. dry with materialdried over Na2SO4
  13. filtrationfiltered
  14. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-de7538987c0d4adb8a6401e4a369f351
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07473784B2

반응 노트

불러오는 중…