Acetic Anhydride → HCID 68933078, compound

HRID 81935Notes

Reaction equation

HRID 81935 reaction equation
[F:1][C:2]([CH3:20])([CH3:19])[CH2:3][N:4]1[C:16]2[C:15]3[N:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[CH:8][C:7]=2[N:6]=[C:5]1[CH2:17][OH:18].C(N(CC)CC)C.[C:28](OC(=O)C)(=[O:30])[CH3:29].C([O-])(O)=O.[Na+]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[C:28]([O:18][CH2:17][C:5]1[N:4]([CH2:3][C:2]([F:1])([CH3:20])[CH3:19])[C:16]2[C:15]3[N:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[CH:8][C:7]=2[N:6]=1)(=[O:30])[CH3:29]

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 68936676[1-(2-fluoro-2-methylpropyl)-1H-imidazo[4,5-c][1,5]naphthyridin-2-yl]methanol

Product 1

HCID 68933078HCID 68933078, compoundYield 90.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of [1-(2-fluoro-2-methylpropyl)-1H-imidazo[4,5-c][1,5]naphthyridin-2-yl]methanol (1.53 g, 5.58 mmol) dissolved in 50 mL of CH2Cl2 was treated with triethylamine (1.55 mL, 11.2 mmol), acetic anhydride (663 μL, 6.70 mmol), and 10 mg of 4-(dimethylamino)pyridine (DMAP). After stirring for 2 hours, the reaction mixture was treated with saturated NaHCO3 solution and the layers were separated. The organic portion was washed successively with 3.5% NaH2PO4 solution, H2O and brine. The organic portion was dried over Na2SO4, filtered and concentrated under reduced pressure. Chromatography (SiO2, 40-60% acetone/hexanes) gave 1.59 g of [1-(2-fluoro-2-methylpropyl)-1H-imidazo[4,5-c][1,5]naphthyridin-2-yl]methyl acetate as an off-white powder.

Workup

  1. customthe layers were separated
  2. washThe organic portion was washed successively with 3.5% NaH2PO4 solution, H2O and brine
  3. dry with materialThe organic portion was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a47a63c6f0dd476aa1de0d8e734ebe01
Source dataset
uspto-grants-2014_09
Patent number
US08846710B2

Reaction notes

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