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Potassium Carbonate → 6-(4-(2-fluorophenyl)oxazol-5-yl)-N-isopropylthiazolo[4,5-c]pyridin-2-amine

HRID 1671803
Notes
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Reaction equation

HRID 1671803 reaction equation
[CH:1]([NH:4][C:5]1[S:6][C:7]2[CH:12]=[C:11]([CH:13]=[O:14])[N:10]=[CH:9][C:8]=2[N:15]=1)([CH3:3])[CH3:2].[F:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH:23]([N+:34]#[C-:35])S(C1C=CC(C)=CC=1)(=O)=O.C([O-])([O-])=O.[K+].[K+]>CCO>[F:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23]1[N:34]=[CH:35][O:14][C:13]=1[C:11]1[N:10]=[CH:9][C:8]2[N:15]=[C:5]([NH:4][CH:1]([CH3:3])[CH3:2])[S:6][C:7]=2[CH:12]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 467382311-Fluoro-2-(isocyano(tosyl)methyl)benzeneHCID 575272142-(Isopropylamino)thiazolo[4,5-c]pyridine-6-carbaldehyde

Product 1

HCID 159874866-(4-(2-fluorophenyl)oxazol-5-yl)-N-isopropylthiazolo[4,5-c]pyridin-2-amineYield 29.3%

Reagents, catalysts & solvents 1

HCID 702
Ethanol
Solvent

Procedure

A solution of 2-(isopropylamino)thiazolo[4,5-c]pyridine-6-carbaldehyde (presumed 0.234 mmol, 1.0 eq.), 1-fluoro-2-(isocyano(tosyl)methyl)benzene (0.079 g, 0.273 mmol, 1.2 eq.), and K2CO3 (0.0654 g, 0.473 mmol, 2.0 eq.) in EtOH (2.4 mL) was refluxed for 4.75 hr. 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 6-(4-(2-fluorophenyl)oxazol-5-yl)-N-isopropylthiazolo[4,5-c]pyridin-2-amine as a light yellow solid (0.0243 g, 29% yield). LC/MS (MH)=355.16.

Workup

  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

Sources & evidence

ORD record
ord-f2926385d59e4a6f8d5dd7f02a95854d
Source dataset
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07994337B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes