1-Propanol → 2-Amino-5-(6-piperidin-1-ylpyridin-3-yl)thiophene-3-carboxamide

HRID 386137Notes

Reaction equation

HRID 386137 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:9]2[CH:10]=[N:11][C:12]([N:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)=[CH:13][CH:14]=2)=[CH:5][C:6]=1[C:7]#[N:8].C([OH:24])CC.[OH-].[Na+]>C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>[NH2:1][C:2]1[S:3][C:4]([C:9]2[CH:10]=[N:11][C:12]([N:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)=[CH:13][CH:14]=2)=[CH:5][C:6]=1[C:7]([NH2:8])=[O:24]

Participants

6

Reactant 3

HCID 10311-PropanolHCID 14798Sodium HydroxideHCID 686708422-Amino-5-(6-piperidin-1-ylpyridin-3-yl)thiophene-3-carbonitrile

Product 1

HCID 595260802-Amino-5-(6-piperidin-1-ylpyridin-3-yl)thiophene-3-carboxamide

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
130 °C

Procedure

Into a microwave vial was added 2-amino-5-(6-piperidin-1-ylpyridin-3-yl)thiophene-3-carbonitrile (225 mg, 0.79 mmol), 1-propanol (6.2 ml), and 25% sodium hydroxide (1.8 ml) and the mixture was heated in the microwave to 130° C. for 30 min. The reaction mixture was diluted with ethyl acetate and sodium bicarbonate to neutralize, extracted with ethyl acetate (3×100 mL), dried over magnesium sulfate, filtered and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with ethyl acetate/methanol to afford the title compound as a solid.

Workup

  1. extractionextracted with ethyl acetate (3×100 mL)
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel
  6. washeluting with ethyl acetate/methanol

Sources & evidence

ORD record
ord-0cf307b4e07245a089331605fc50d76d
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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