Dibah → HCID 57527233, compound

HRID 1671797Notes

Reaction equation

HRID 1671797 reaction equation
[CH:1]([NH:4][C:5]1[S:6][C:7]2[C:8]([N:18]=1)=[N:9][CH:10]=[C:11]([C:13](OCC)=[O:14])[CH:12]=2)([CH3:3])[CH3:2].CC(C[Al]CC(C)C)C>C1(C)C=CC=CC=1.C1COCC1>[CH:1]([NH:4][C:5]1[S:6][C:7]2[C:8]([N:18]=1)=[N:9][CH:10]=[C:11]([CH2:13][OH:14])[CH:12]=2)([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 16682954Dibah2×HCID 57527167HCID 57527167, compound

Product 1

HCID 57527233HCID 57527233, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-(isopropylamino)thiazolo[4,5-b]pyridine-6-carboxylate (0.278 g, 1.05 mmol) in toluene (10 mL) and THF (5 mL) was introduced Dibal-H (5.8 mL, 5.8 mmol) at −78° C. over 10 min. The resulting mixture was allowed to warm to rt and stirred for 4 hr. Additional Dibal-H (1.2 mL, 1.2 mmol) was added at rt, and the mixture was stirred for additional 1.5 hr before it was poured into ice-cold water (100 mL). The mixture was stirred at rt for 30 min, and then filtered through Celite® 545. The organic layer of filtrate was separated. The aqueous layer was basified with saturated NaHCO3 solution and extracted with AcOEt. The combined organic phase was washed with brine and dried over anhydrous MgSO4. Evaporation of solvent under vacuum gave the title compound as a viscous oil.

Workup

  1. stirringthe mixture was stirred for additional 1.5 hr before it
  2. stirringThe mixture was stirred at rt for 30 min
  3. filtrationfiltered through Celite® 545
  4. customThe organic layer of filtrate was separated
  5. extractionextracted with AcOEt
  6. washThe combined organic phase was washed with brine
  7. dry with materialdried over anhydrous MgSO4
  8. customEvaporation of solvent under vacuum

Sources & evidence

ORD record
ord-f25b369ffb91472799196bf430b1a4f3
Source dataset
uspto-grants-2011_08
Patent number
US07994337B2

Reaction notes

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