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

HRID 1671813ノート

反応式

HRID 1671813 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8feb1f9bc5054b0ebc4b85bb1b2bbb7b
出典データセット
uspto-grants-2011_08
特許番号
US07994337B2

反応ノート

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