Sodium Acetate → HCID 57742965, compound

HRID 1801979Notes

Reaction equation

HRID 1801979 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[N:7][CH:8]=[C:9]([I:12])[CH:10]=2)[N:5]([CH3:13])[C:4](=[O:14])[C:3]=1[C:15](=[O:22])[CH2:16][CH2:17][C:18]([O:20]C)=[O:19].C(OC1C2C(=NC=C(I)C=2)N(C)C(=O)C=1)(=O)CCC(OC)=O.C([O-])(=O)C.[Na+]>>[OH:1][C:2]1[C:11]2[C:6](=[N:7][CH:8]=[C:9]([I:12])[CH:10]=2)[N:5]([CH3:13])[C:4](=[O:14])[C:3]=1[C:15](=[O:22])[CH2:16][CH2:17][C:18]([OH:20])=[O:19]

Participants

4

Reactant 3

HCID 517045Sodium AcetateHCID 67406545HCID 67406545, compoundHCID 67407443HCID 67407443, compound

Product 1

HCID 57742965HCID 57742965, compoundYield 27%

Conditions

Temperature
140 °C

Procedure

Methyl 4-(4-hydroxy-6-iodo-1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl)-4-oxobutanoate. A mixture of 6-iodo-1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-4-yl methyl succinate (0.096 g, 0.23 mmol) and sodium acetate (0.019 g, 0.23 mmol) was heated at 140° C. for 5 minutes. The reaction was cooled to room temperature and the solids rinsed with DCM. The filtrate was purified by flash chromatography using EtOAc/hexane to afford the title compound in 27% yield. 1H-NMR (300 MHz, CDCl3) δ ppm 8.85 (1H, d, J=2.3 Hz), 8.71 (1H, d, J=2.2 Hz), 3.72 (3H, s), 3.71 (3H, s), 3.65 (2H, t, J=6.3 Hz), 2.73 (2H, t, J=6.3 Hz). MS m/z: 417 (M+).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. washthe solids rinsed with DCM
  3. customThe filtrate was purified by flash chromatography

Sources & evidence

ORD record
ord-91fe8aecc19a4306a99460691828ec04
Source dataset
uspto-grants-2013_01
Patent number
US08349868B2

Reaction notes

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