Hydrogen Bromide → 4-hydroxy-N,N,2-trimethyl-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridine-1-carboxamide

HRID 1817349Notes

Reaction equation

HRID 1817349 reaction equation
C[O:2][C:3]1[C:4](=[O:29])[N:5]([CH3:28])[C:6]([C:23]([N:25]([CH3:27])[CH3:26])=[O:24])=[C:7]2[C:12]=1[C:11](=[O:13])[N:10](CC1C=CC(OC)=CC=1)[CH2:9][CH2:8]2.Br>CC(O)=O>[OH:2][C:3]1[C:4](=[O:29])[N:5]([CH3:28])[C:6]([C:23]([N:25]([CH3:26])[CH3:27])=[O:24])=[C:7]2[C:12]=1[C:11](=[O:13])[NH:10][CH2:9][CH2:8]2

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 690582414-methoxy-6-(4-methoxybenzyl)-N,N,2-trimethyl-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridine-1-carboxamide

Product 1

HCID 690584564-hydroxy-N,N,2-trimethyl-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridine-1-carboxamide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
75 °C

Procedure

In a 50 mL heavy walled glass pressure flask 4-methoxy-6-(4-methoxybenzyl)-N,N,2-trimethyl-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridine-1-carboxamide (3.9 g) and 15 ml of (commercial) 33% HBr in HOAc were mixed. The flask was sealed, heated to 75° C. and allowed to stir overnight. The solvent was removed in vacuo. The remaining oil was dissolved in CH3CN and purified by reverse phase on a Biotage KPCM 250 compression module containing a 10 cm×60 cm Kiloprep cartridge. The product elutes at 13% CH3CN in water containing 0.1% TFA.

Workup

  1. additionwere mixed
  2. customThe flask was sealed
  3. customThe solvent was removed in vacuo
  4. dissolutionThe remaining oil was dissolved in CH3CN
  5. custompurified by reverse phase on a Biotage KPCM 250 compression module
  6. additioncontaining a 10 cm×60 cm Kiloprep cartridge

Sources & evidence

ORD record
ord-b0a5058bb4794737a75faa86d229e729
Source dataset
uspto-grants-2009_10
Patent number
US07598264B2

Reaction notes

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