HCID 69654916, compound → HCID 69654494, compound

HRID 1244052Notes

Reaction equation

HRID 1244052 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[CH:5]=[CH:6][C:7]1[C:8]([N+:20]([O-])=O)=[N:9][C:10]([CH:15]2[O:19][CH2:18][CH2:17][O:16]2)=[C:11]([O:13][CH3:14])[CH:12]=1)[CH3:2]>C(O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:23])[CH2:5][CH2:6][C:7]1[C:8]([NH2:20])=[N:9][C:10]([CH:15]2[O:19][CH2:18][CH2:17][O:16]2)=[C:11]([O:13][CH3:14])[CH:12]=1)[CH3:2]

Participants

4

Reactant 1

HCID 69654916HCID 69654916, compound

Product 1

HCID 69654494HCID 69654494, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The oil isolated in step 5 was dissolved in 30 ml of ethanol and hydrogenated for 90 minutes at 50 PSI using 10% Pd/C as the catalyst. The reaction mixture was filtered and evaporated to yield the intermediate 3-(2-amino-6-[1,3]dioxolan-2-yl-5-methoxy-pyridin-3-yl)-propionic acid ethyl ester as a dark oil. Mass Spectrum: m/e=297.1 (p+1). This material was dissolved in 10 ml of toluene and heated to reflux for 4 hours. The solution was cooled to room temperature and evaporated to yield 0.1 g of 7-[1,3]dioxolan-2-yl-6-methoxy-3,4-dihydro-1H-[1,8]naphthyridin-2-one as a dark oil. Mass spectrum: m/e=251 (p+1). 1H NMR (CDCl3) δ 7.10 (s, 1H), 6.10 (s, 1H), 4.30 (m, 2H), 4.10 (m, 2H), 3.90 (s, 3H), 2.90 (m, 2H), 2.75 (m, 2H). This material was used without further purification in step 7.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customevaporated

Sources & evidence

ORD record
ord-c6a856f641b147f89e49230c0d8938ac
Source dataset
uspto-grants-2006_10
Patent number
US07119207B2

Reaction notes

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