Morpholine → HCID 45376602, compound

HRID 1991455Notes

Reaction equation

HRID 1991455 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[N:6][C:7]([CH3:16])=[C:8]([O:12][CH2:13][CH2:14]Cl)[C:9]=2[CH3:11])[S:4][C:3]=1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].C([O-])([O-])=O.[K+].[K+].[NH:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1>CC#N>[NH2:1][C:2]1[C:10]2[C:5](=[N:6][C:7]([CH3:16])=[C:8]([O:12][CH2:13][CH2:14][N:30]3[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)[C:9]=2[CH3:11])[S:4][C:3]=1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 59129745HCID 59129745, compound

Product 1

HCID 45376602HCID 45376602, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

tert-Butyl 3-amino-5-(2-chloroethoxy)-4,6-dimethyl-thieno[2,3-b]pyridine-2-carboxylate, prepared above (50 mg, 0.22 mmol), was dissolved in CH3CN (5 mL), followed by the addition of K2CO3 (41 mg, 0.30 mmol), morpholine (26 mg, 0.30 mmol) and a catalytic amount of KI. The mixture was heated to reflux overnight, the solvent was removed under reduced pressure, water was added and the residue was extracted with ethyl acetate (10 mL), and the organic phases were washed with water (5 mL×3), brine, dried over anhydrous Na2SO4, concentrated and purified by preparative HPLC to furnish the title compound, tert-butyl 3-amino-4,6-dimethyl-5-(2-morpholin-4-yl-ethoxy)-thieno[2,3-b]pyridine-2-carboxylate (20 mg, 30%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux overnight
  3. customthe solvent was removed under reduced pressure, water
  4. additionwas added
  5. extractionthe residue was extracted with ethyl acetate (10 mL)
  6. washthe organic phases were washed with water (5 mL×3), brine
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated
  9. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-32a5e532dca24bbe9a93ad3ab3bf4a36
Source dataset
uspto-grants-2010_01
Patent number
US07645881B2

Reaction notes

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