Ethyl Acetate → HCID 58094803, compound

HRID 2282261Notes

Reaction equation

HRID 2282261 reaction equation
Br[CH:2]([C:6]1[S:7][C:8]([C:17]2[N:21]=[CH:20][N:19]([CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][O:23]3)[N:18]=2)=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:10]=1)[C:3]([CH3:5])=O.[NH2:28][C:29]1[CH:34]=[CH:33][C:32]([Br:35])=[CH:31][N:30]=1.C(=O)(O)[O-].[Na+].CCOC(C)=O>C1COCC1.CC(O)C>[Br:35][C:32]1[CH:33]=[CH:34][C:29]2[N:30]([C:2]([C:6]3[S:7][C:8]([C:17]4[N:21]=[CH:20][N:19]([CH:22]5[CH2:27][CH2:26][CH2:25][CH2:24][O:23]5)[N:18]=4)=[C:9]([C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=4)[N:10]=3)=[C:3]([CH3:5])[N:28]=2)[CH:31]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 706222-Amino-5-bromopyridineHCID 516892Sodium BicarbonateHCID 86649612HCID 86649612, compound

Product 1

HCID 58094803HCID 58094803, compoundYield 15.1%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1-bromo-1-{4-phenyl-5-[1-(tetrahydro-2H-pyran-2-yl)-1H-1,2,4-triazol-3-yl]-1,3-thiazol-2-yl}acetone (2.96 g, 6.6 mmol) obtained in Example 116-B(vi) in THF (33 mL) and 2-propanol (33 mL), was added 2-amino-5-bromopyridine (5.71 g, 33.0 mmol), and the mixture was stirred at 80° C. for 3 h. The reaction mixture was allowed to cool to rt, and then were added saturated aqueous solution of sodium bicarbonate (60 mL) and EtOAc (150 mL). The aqueous layer was extracted with EtOAc (80 mL), and the combined organic layer was dried over anhydrous magnesium sulfate. Insoluble materials were removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (EtOAc/hexane=20/80→100/0; then MeOH/EtOAc=20/80), and then basic silica gel column chromatography (EtOAc/hexane=10/90→80/20) to give the title compound (520 mg, 15%) as a pale yellow solid.

Workup

  1. temperatureto cool to rt
  2. extractionThe aqueous layer was extracted with EtOAc (80 mL)
  3. dry with materialthe combined organic layer was dried over anhydrous magnesium sulfate
  4. customInsoluble materials were removed by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (EtOAc/hexane=20/80→100/0

Sources & evidence

ORD record
ord-1a707b0e7aea4fc9b4db081c7d88f16f
Source dataset
uspto-grants-2015_09
Patent number
US09139589B2

Reaction notes

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