Hydrochloric Acid → Methyl 6-(4-fluorobenzyl)-4-hydroxy-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxylate

HRID 1817294Notes

Reaction equation

HRID 1817294 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][CH:10]=[CH:9][C:8]2=[O:13])=[CH:4][CH:3]=1.C[O:17][C:18]1O[C:21]([C:23]([O:25][CH3:26])=[O:24])=[N:20][CH:19]=1.Cl>CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][C:10]3[C:21]([C:23]([O:25][CH3:26])=[O:24])=[N:20][CH:19]=[C:18]([OH:17])[C:9]=3[C:8]2=[O:13])=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1491126Methyl 5-methoxy-1,3-oxazole-2-carboxylateHCID 69064745HCID 69064745, compound

Product 1

HCID 69062288Methyl 6-(4-fluorobenzyl)-4-hydroxy-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
120 °C

Procedure

In a sealed tube, 1-(4-fluorobenzyl)-5,6-dihydropyridin-2-(1H)-one (3.84 g, 18.7 mmol), and methyl 5-methoxy-1,3-oxazole-2-carboxylate prepared in Step 5 (2.94 g, 18.7 mmol), were combined. The reaction mixture was heated at 120° C. After 24 hours, the resultant mixture was cooled and methanol saturated with HCl (2 mL) was added. The product mixture stirred at room temperature for 40 minutes, then was concentrated under vacuum. The residual crude material was diluted with DMSO (6.0 mL) and filtered to give the title compound.

Workup

  1. concentrationwas concentrated under vacuum
  2. additionThe residual crude material was diluted with DMSO (6.0 mL)
  3. filtrationfiltered

Sources & evidence

ORD record
ord-187951accfdc4634834b0c04bc955b82
Source dataset
uspto-grants-2009_10
Patent number
US07598264B2

Reaction notes

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