Acetic Anhydride → 1-[(Dimethylamino)carbonyl]-4-methoxy-6-(4-methoxybenzyl)-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridin-3-yl acetate

HRID 1817346Notes

Reaction equation

HRID 1817346 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[N+:5]([O-])[C:6]([C:23]([N:25]([CH3:27])[CH3:26])=[O:24])=[C:7]2[C:12]=1[C:11](=[O:13])[N:10]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)[CH2:9][CH2:8]2.[C:29]([O:32]C(=O)C)(=[O:31])[CH3:30]>>[C:29]([O:32][C:4]1[N:5]=[C:6]([C:23]([N:25]([CH3:27])[CH3:26])=[O:24])[C:7]2[CH2:8][CH2:9][N:10]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[C:11](=[O:13])[C:12]=2[C:3]=1[O:2][CH3:1])(=[O:31])[CH3:30]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 690604854-methoxy-6-(4-methoxybenzyl)-N,N-dimethyl-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxamide 2-oxide

Product 1

HCID 690652291-[(Dimethylamino)carbonyl]-4-methoxy-6-(4-methoxybenzyl)-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridin-3-yl acetate

Conditions

Temperature
100 °C

Procedure

4-methoxy-6-(4-methoxybenzyl)-N,N-dimethyl-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxamide 2-oxide (10.3 g) was dissolved in 30 ml acetic anhydride and transferred to a 50 mL heavy walled pressure flask and sealed. The reaction was heated in a 100° C. oil bath overnight. The reaction was concentrated in vacuo. The remaining oil was dissolved in 5 mL EtOAc and purified on an Isco automated system affixed with a Biotage Flash 40 (L) (120 g silica) cartridge eluted with 0-10% MeOH in EtOAc over 20 minutes and hold at 10% for 40 minutes. The product eluted pure by HPLC/MS and NMR.

Workup

  1. customtransferred to a 50 mL heavy walled pressure flask
  2. customsealed
  3. concentrationThe reaction was concentrated in vacuo
  4. dissolutionThe remaining oil was dissolved in 5 mL EtOAc
  5. custompurified on an Isco automated system
  6. washeluted with 0-10% MeOH in EtOAc over 20 minutes
  7. washThe product eluted pure by HPLC/MS and NMR

Sources & evidence

ORD record
ord-b7fd32f2e3b24ce490a1c2f3a4296df5
Source dataset
uspto-grants-2009_10
Patent number
US07598264B2

Reaction notes

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