HCID 67256279, compound → HCID 67257668, compound

HRID 1509332Notes

Reaction equation

HRID 1509332 reaction equation
[N+:1]([C:4]1[C:9](=[O:10])[NH:8][C:7]([C:11]2[CH:16]=[CH:15][C:14]([C:17]3([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:20][CH2:19][CH2:18]3)=[CH:13][CH:12]=2)=[C:6]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:5]=1)([O-])=O>C(O)(=O)C.[Zn]>[C:24]([O:23][C:22](=[O:28])[NH:21][C:17]1([C:14]2[CH:15]=[CH:16][C:11]([C:7]3[NH:8][C:9](=[O:10])[C:4]([NH2:1])=[CH:5][C:6]=3[C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)=[CH:12][CH:13]=2)[CH2:18][CH2:19][CH2:20]1)([CH3:27])([CH3:25])[CH3:26]

Participants

4

Reactant 1

HCID 67256279HCID 67256279, compound

Product 1

HCID 67257668HCID 67257668, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Tert-butyl (1-(4-(5-nitro-6-oxo-3-phenyl-1,6-dihydropyridin-2-yl)phenyl)cyclobutyl)carbamate (10.95 g, 23.77 mmol) was dissolved in acetic acid (250 mL) at room temperature. Zinc powder (10 g, 153 mmol) was added at 30° C. and the resulting suspension was stirred at room temperature for 18 hours. The reaction mixture was concentrated under reduced pressure and the obtained residue was partitioned between water (250 mL) and ethyl acetate (250 mL). The aqueous phase was extracted with fresh ethyl acetate (3×200 mL) and the combined organic layers were washed with water (200 mL), brine (200 mL), dried on anhydrous Na2SO4, filtered and concentrated to dryness under reduced pressure. The obtained crude was purified by Biotage silica gel chromatography (gradient 0% to 3% methanol in dichloromethane) to give the title compound (4.3 g, 43%). It was used for the next step without further purification. LCMS (Method A) RT 5.96 min, M+1=432.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe obtained residue was partitioned between water (250 mL) and ethyl acetate (250 mL)
  3. extractionThe aqueous phase was extracted with fresh ethyl acetate (3×200 mL)
  4. washthe combined organic layers were washed with water (200 mL), brine (200 mL)
  5. dry with materialdried on anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure
  8. customThe obtained crude
  9. customwas purified by Biotage silica gel chromatography (gradient 0% to 3% methanol in dichloromethane)

Sources & evidence

ORD record
ord-1b1a917744c942fdb0efe395842dd162
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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