HCID 46908774, compound → HCID 66746289, compound

HRID 1961480Notes

Reaction equation

HRID 1961480 reaction equation
[C:1]([C:5]1[CH:25]=[CH:24][C:8]([CH2:9][NH:10][C:11]([C:13]2[C:14]([CH3:23])=[N:15][C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[CH:18][N:17]=3)=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:26][Mg]Br>C1COCC1>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][NH:10][C:11]([C:13]2[C:14]([CH3:23])=[N:15][C:16]3[C:21]([C:22]=2[CH3:26])=[CH:20][CH:19]=[CH:18][N:17]=3)=[O:12])=[CH:24][CH:25]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 46908774HCID 46908774, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 66746289HCID 66746289, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-(4-tert-butylbenzyl)-2-methyl-1,8-naphthyridine-3-carboxamide (150 mg, 0.45 mmol) was dissolved in THF (anh, 8.0 ml) under N2. Methylmagnesium bromide (4.5 ml of a 1M sln) was added dropwise. The mixture was stirred at r.t. for 2.0 h. The reaction was quenched with NH4Cl (sat). The product was extracted with EtOAc, dried (MgSO4), filtered and concentrated. The residue was dissolved in CHCl3 and O2 (94%) was bubbled through the solution for 3.0 h. The mixture was concentrated and purified by flash chromatography CH2Cl2/MeOH (96:4→95:5) yielding 50.0 mg of the title compound (32%). 1H NMR (CDCl3) δ 8.80 (m, 1H), 8.13 (m, 1H), 7.44 (d, 2H), 7.41 (d, 2H), 7.35 (m, 1H), 7.02 (t, 1H), 4.74 (d, 2H), 2.73 (s, 3H), 2.49 (s, 3H), 1.34 (s, 9H).

Workup

  1. customThe reaction was quenched with NH4Cl (sat)
  2. extractionThe product was extracted with EtOAc
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in CHCl3
  7. customO2 (94%) was bubbled through the solution for 3.0 h
  8. concentrationThe mixture was concentrated
  9. custompurified by flash chromatography CH2Cl2/MeOH (96:4→95:5)

Sources & evidence

ORD record
ord-bd0538b662c64ed0a312f41c2caed84d
Source dataset
uspto-grants-2013_04
Patent number
US08415333B2

Reaction notes

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