Hydrochloric Acid → HCID 69056896, compound

HRID 1817317Notes

Reaction equation

HRID 1817317 reaction equation
[C:1]([N:4]([C:8]1[N:9]([CH3:30])[C:10](=[O:29])[C:11]([O:27][CH3:28])=[C:12]2[C:17]=1[CH2:16][CH2:15][N:14]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)[C:13]2=[O:26])C(=O)C)(=[O:3])[CH3:2].C[O-].[Na+].Cl>CO>[F:25][C:22]1[CH:21]=[CH:20][C:19]([CH2:18][N:14]2[CH2:15][CH2:16][C:17]3[C:12](=[C:11]([O:27][CH3:28])[C:10](=[O:29])[N:9]([CH3:30])[C:8]=3[NH:4][C:1](=[O:3])[CH3:2])[C:13]2=[O:26])=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 69059585HCID 69059585, compound

Product 1

HCID 69056896HCID 69056896, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To N-acetyl-N-[6-(4-fluorobenzyl)-4-methoxy-2-methyl-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridin-1-yl]acetamide (0.149 g, 0.36 mmol) in MeOH (5 mL) cooled to 0° C. was added 30% weight solution NaOMe in MeOH (0.2 mL, 1.07 mmol). The reaction was warmed to room temperature for 40 minutes, then 1 N HCl was added (1.07 mL) and the reaction was concentrated, and CHCl3 and 10% KHSO4 were added. The layers were separated and the aqueous was extracted repeatedly. The organic layer was dried over Na2SO4, filtered, combined with the collected solid and evaporated to give the crude product.

Workup

  1. concentrationthe reaction was concentrated
  2. additionCHCl3 and 10% KHSO4 were added
  3. customThe layers were separated
  4. extractionthe aqueous was extracted repeatedly
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-1e9346ae232842eb97ae65599a0967d0
Source dataset
uspto-grants-2009_10
Patent number
US07598264B2

Reaction notes

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