7-(Methyloxy)-1-[(2R)-2-oxiranylmethyl]-3,4-dihydro-1,8-naphthyridin-2(1H)-one → (15)-1-(hydroxymethyl)-1,2,5,6-tetrahydro-4H,9H-imidazo[1,2,3-ij]-1,8-naphthyridine-4,9-dione

HRID 420671Notes

Reaction equation

HRID 420671 reaction equation
C[O:2][C:3]1[N:12]=[C:11]2[C:6]([CH2:7][CH2:8][C:9](=[O:17])[N:10]2[CH2:13][C@@H:14]2[CH2:16][O:15]2)=[CH:5][CH:4]=1>CN(C=O)C>[OH:15][CH2:16][C@H:14]1[N:12]2[C:11]3[N:10]([C:9](=[O:17])[CH2:8][CH2:7][C:6]=3[CH:5]=[CH:4][C:3]2=[O:2])[CH2:13]1

Participants

3

Reactant 1

HCID 580017637-(Methyloxy)-1-[(2R)-2-oxiranylmethyl]-3,4-dihydro-1,8-naphthyridin-2(1H)-one

Product 1

HCID 58200906(15)-1-(hydroxymethyl)-1,2,5,6-tetrahydro-4H,9H-imidazo[1,2,3-ij]-1,8-naphthyridine-4,9-dioneYield 31%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 7-(methyloxy)-1-[(2R)-2-oxiranylmethyl]-3,4-dihydro-1,8-naphthyridin-2(1H)-one (1.167 g, 4.98 mmol) in DMF (20 ml) under argon was heated to 120° C. for 6 h. Reaction was then evaporated and chromatographed (0-20% MeOH/DCM) to give product as an orange solid (339 mg, 31%).

Workup

  1. customReaction
  2. customwas then evaporated
  3. customchromatographed (0-20% MeOH/DCM)

Sources & evidence

ORD record
ord-bb62c4def1c548bab068d03549a5963c
Source dataset
uspto-grants-2012_01
Patent number
US08097628B2

Reaction notes

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