Sodium Methoxide → HCID 57525458, compound

HRID 646977Notes

Reaction equation

HRID 646977 reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH2:10][CH2:11][CH:12]2[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)[N:5]=[CH:4][C:3]=1[C:19]1[NH:23]C2C=CC(F)=C(C)C=2N=1.[CH3:30][O-:31].[Na+]>CO>[CH3:30][O:31][C:2]1[C:3]([C:19]#[N:23])=[CH:4][N:5]=[C:6]([O:8][CH2:9][CH2:10][CH2:11][CH:12]2[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)[CH:7]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 11362059HCID 11362059, compound

Product 1

HCID 57525458HCID 57525458, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-chloro-6-[3-(1-methyl-piperidin-4-yl)-propoxy]-nicotinonitrile (Example 115) in methanol (0.2 M) was treated with sodium methoxide (4 equiv) at reflux temperature for 4 h. The mixture was cooled to rt, diluted with satd. aq. NaHCO3, and extracted with chloroform. The organic extract was dried (Na2SO4), filtered, and concentrated to yield 4-methoxy-6-[3-(1-methyl-piperidin-4-yl)-propoxy]-nicotinonitrile (100%). This intermediate was converted to the title compound according to Example 115. MS (electrospray): mass calculated for C23H30ClN4O2, 394.24. m/z found, 395.4 [M+H]+.

Workup

  1. temperatureat reflux temperature for 4 h
  2. additiondiluted with satd
  3. extractionaq. NaHCO3, and extracted with chloroform
  4. extractionThe organic extract
  5. dry with materialwas dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b011e982d6354400ba9753a0ea40e219
Source dataset
uspto-grants-2010_04
Patent number
US07705149B2

Reaction notes

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