Sodium Methoxide → HCID 66774227, compound

HRID 255291Notes

Reaction equation

HRID 255291 reaction equation
Cl[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][N:11]=1)[N:8]([CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][CH:17]([NH:20]C(=O)OC(C)(C)C)[CH2:16][CH2:15]1)[C:7](=[O:28])[CH:6]=[CH:5]2.[CH3:29][O-:30].[Na+]>CO.O.C(OCC)(=O)C>[NH2:20][CH:17]1[CH2:16][CH2:15][N:14]([CH2:13][CH2:12][N:8]2[C:9]3[C:4](=[CH:3][C:2]([O:30][CH3:29])=[N:11][CH:10]=3)[CH:5]=[CH:6][C:7]2=[O:28])[CH2:19][CH2:18]1

Participants

6

Reactant 2

HCID 10942334Sodium MethoxideHCID 86642638HCID 86642638, compound2×

Product 1

HCID 66774227HCID 66774227, compoundYield 64%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

A solution of tert-butyl {1-[2-(6-chloro-2-oxo-1,7-naphthyridin-1(2H)-yl)ethyl]piperidin-4-yl}carbamate (Intermediate 129, 335 mg, 0.83 mmol) was treated with a solution of sodium methoxide in methanol (0.5 M, 4 mL). The reaction was sealed in a tube and heated at 150° C. for 4 hours using microwave irradiation. The reaction was diluted with water and ethyl acetate. The layers were separated. The aqueous phase was washed with ethyl acetate twice. The organic extracts were combined dried over magnesium sulfate and evaporated at reduced pressure to give 116 mg (64%) of the crude product as a yellow oil.

Workup

  1. customThe reaction was sealed in a tube
  2. custommicrowave irradiation
  3. customThe layers were separated
  4. washThe aqueous phase was washed with ethyl acetate twice
  5. dry with materialThe organic extracts were combined dried over magnesium sulfate
  6. customevaporated at reduced pressure

Sources & evidence

ORD record
ord-8f47003983864dc6ba210a9b7d336967
Source dataset
uspto-grants-2011_01
Patent number
US07875715B2

Reaction notes

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