Sodium Methoxide → HCID 59212295, compound

HRID 2243859Notes

Reaction equation

HRID 2243859 reaction equation
Cl[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:14]3[CH:15]=[C:16]([NH:21][C:22](=[O:29])[C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH:17]=[CH:18][C:19]=3[CH3:20])[C:8](=[O:13])[N:9]2[CH3:12])=[CH:4][N:3]=1.[CH3:30][O-:31].[Na+]>CO>[CH3:30][O:31][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:14]3[CH:15]=[C:16]([NH:21][C:22](=[O:29])[C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH:17]=[CH:18][C:19]=3[CH3:20])[C:8](=[O:13])[N:9]2[CH3:12])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 59212363HCID 59212363, compound

Product 1

HCID 59212295HCID 59212295, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

N-(3-(7-chloro-1,2-dihydro-1-methyl-2-oxo-1,6-naphthyridin-3-yl)-4-methylphenyl)benzamide A6 (70 mg, 0.17 mmol) is treated with sodium methoxide (0.8 mL of a 0.5 M solution in methanol) and heated to 65° C. for 3 h. The reaction is cooled to rt and partitioned with EtOAc and aqueous ammonium chloride. The organic layer is washed with brine, dried over magnesium sulfate, filtered and solvent removed. Crude product is dissolved in DMF (1 mL) and purified by preparative LCMS to afford the desired product. 1H NMR 400 MHz (MeOD) δ 8.56 (s, 1H), 7.92 (d, J=8 Hz, 2H), 7.88 (s, 1H), 7.64-7.46 (m, 5H), 7.28 (d, J=8 Hz, 1H), 6.84 (1H), 4.05 (s, 3H), 3.71 (s, 3H), 2.20 (s, 3H); MS m/z 400.2 (M+1).

Workup

  1. temperatureThe reaction is cooled to rt
  2. custompartitioned with EtOAc and aqueous ammonium chloride
  3. washThe organic layer is washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customsolvent removed
  7. dissolutionCrude product is dissolved in DMF (1 mL)
  8. custompurified by preparative LCMS

Sources & evidence

ORD record
ord-522b578401f04527b6160bd8fa5919ee
Source dataset
uspto-grants-2010_03
Patent number
US07678792B2

Reaction notes

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