Cyclohexanemethylamine → 4-(2-(cyclohexylmethylamino)benzo[d]oxazol-6-yloxy)-N-methylpyridine-2-carboxamide

HRID 1988413Notes

Reaction equation

HRID 1988413 reaction equation
CS([C:4]1[O:5][C:6]2[CH:12]=[C:11]([O:13][C:14]3[CH:19]=[CH:18][N:17]=[C:16]([C:20]([NH:22][CH3:23])=[O:21])[CH:15]=3)[CH:10]=[CH:9][C:7]=2[N:8]=1)=O.[CH:24]1([CH2:30][NH2:31])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1>C1COCC1>[CH:24]1([CH2:30][NH:31][C:4]2[O:5][C:6]3[CH:12]=[C:11]([O:13][C:14]4[CH:19]=[CH:18][N:17]=[C:16]([C:20]([NH:22][CH3:23])=[O:21])[CH:15]=4)[CH:10]=[CH:9][C:7]=3[N:8]=2)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

4

Reactant 2

HCID 76688CyclohexanemethylamineHCID 57725414N-methyl-4-(2-(methylsulfinyl)benzo[d]oxazol-6-yloxy)picolinamide

Product 1

HCID 577255594-(2-(cyclohexylmethylamino)benzo[d]oxazol-6-yloxy)-N-methylpyridine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(2-(methylsulfinyl)benzo[d]oxazol-6-yloxy)-N-methylpyridine-2-carboxamide (1.40 g, 4.23 mmol, 1.0 eq) in 15 mL of THF was added cyclohexylmethanamine (955 mg, 8.46 mmol, 2.0 eq) at room temperature. The reaction mixture was stirred at that temperature for 2 hours. After the solvent was removed under reduced pressure, the residue was dissolved in 150 mL of ethyl acetate. The resulting mixture was washed with water (20 mL), brine (20 mL), then dried over MgSO4, filtered, and evaporated under reduced pressure to give crude product, which was purified by silica gel column eluted with ethyl acetate and hexane to give the titled compound. MH+=381.

Workup

  1. customAfter the solvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in 150 mL of ethyl acetate
  3. washThe resulting mixture was washed with water (20 mL), brine (20 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customto give crude product, which
  8. customwas purified by silica gel column
  9. washeluted with ethyl acetate and hexane

Sources & evidence

ORD record
ord-e4b7d7ce443b4d039b1d1f65a7e07c3c
Source dataset
uspto-grants-2009_06
Patent number
US07553854B2

Reaction notes

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