Imidazole → HCID 68629865, compound

HRID 1801473Notes

Reaction equation

HRID 1801473 reaction equation
[F:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[CH2:12][CH:13]([OH:16])[CH2:14][OH:15])=[N:9][C:8]([O:17][CH3:18])=[CH:7][CH:6]=2.N1C=CN=C1.[CH3:24][C:25]([Si:28](Cl)([CH3:30])[CH3:29])([CH3:27])[CH3:26]>C1COCC1.CN(C=O)C.CC(=O)OCC>[C:25]([Si:28]([CH3:30])([CH3:29])[O:15][CH2:14][CH:13]([OH:16])[CH2:12][C:11]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:17][CH3:18])[N:9]=2)[N:4]=[CH:3][C:2]=1[F:1])([CH3:27])([CH3:26])[CH3:24]

Participants

7

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 68639467HCID 68639467, compound

Product 1

HCID 68629865HCID 68629865, compoundYield 87%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of rac-3-(3-fluoro-6-methoxy-[1,5]naphthyridin-4-yl)-propane-1,2-diol (3.6 g, 14.2 mmol, prepared as described in WO 2008/003690) in THF (150 mL) and DMF (10 mL) was treated with imidazole (1.07 g, 1.1 eq.) and a solution of TBDMSCl (2.15 g, 1 eq.) in THF (10 mL) at 0° C., the mixture was stirred at rt for 24 h, diluted with EA and washed with water (2×100 mL) and brine, dried over MgSO4 and concentrated. The residue was purified by CC (Hept/EA 1:1) to give the desired intermediate as a colourless solid (4.5 g, 87% yield).

Workup

  1. washwashed with water (2×100 mL) and brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe residue was purified by CC (Hept/EA 1:1)

Sources & evidence

ORD record
ord-803d7a92480940feafa2836dfab58608
Source dataset
uspto-grants-2013_01
Patent number
US08349828B2

Reaction notes

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