Morpholine → HCID 67025080, compound

HRID 1504766Notes

Reaction equation

HRID 1504766 reaction equation
CS(O[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[N:8]=1)(=O)=O.[NH:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[N:21]1([CH2:6][C:7]2[N:8]=[C:9]([NH:13][C:14](=[O:15])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH:10]=[CH:11][CH:12]=2)[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 19349110(6-(Tert-butoxycarbonylamino)pyridin-2-yl)methyl methanesulfonate

Product 1

HCID 67025080HCID 67025080, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of {6-[(tert-butoxycarbonyl)amino]pyridin-2-yl}methyl methanesulfonate (160 mg, 0.52 mmol) in acetonitrile (2.5 mL) was added morpholine (90 mg, 1.0 mmol) and potassium carbonate (214 mg, 1.55 mmol) at room temperature. After 16 hours, the reaction mixture was quenched with aqueous saturated sodium bicarbonate, partially concentrated under reduced pressure, and diluted with ethyl acetate. The organic layer was separated, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to afford tert-butyl [6-(morpholin-4-ylmethyl)pyridin-2-yl]carbamate that was used without further purification. MS ESI calc'd for C15H24N3O3 [M+H]+ 294. found 294.

Workup

  1. customthe reaction mixture was quenched with aqueous saturated sodium bicarbonate
  2. concentrationpartially concentrated under reduced pressure
  3. additiondiluted with ethyl acetate
  4. customThe organic layer was separated
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fb2552b473274b7fb794c433140a2054
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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