Piperidine → HCID 40012281, compound

HRID 1914547Notes

Reaction equation

HRID 1914547 reaction equation
[Br:1][C:2]1[S:6][CH:5]=[C:4]([C:7]([OH:9])=O)[CH:3]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=N[C:29]2[CH:30]=[CH:31][CH:32]=[N:33][C:28]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.N1CCCCC1>CN(C=O)C>[Br:1][C:2]1[S:6][CH:5]=[C:4]([C:7]([N:33]2[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]2)=[O:9])[CH:3]=1

Participants

6

Reactant 4

HCID 8082PiperidineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 120399785-Bromothiophene-3-carboxylic acid

Product 1

HCID 40012281HCID 40012281, compoundYield 43.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Bromo-thiophene-3-carboxylic acid (150 mg, 0.72 mmol) was dissolved in DMF (3 mL). DIPEA (2.16 mmol), HATU (0.72 mmol) and piperidine (0.72 mmol) were added and the reaction mixture stirred at room temperature for 1 hour. The mixture was partitioned between ethyl acetate and water and the organic solution separated, washed with 1 N hydrochloric acid, dried over magnesium sulfate, filtered and the solvent evaporated. The residue was purified by flash chromatography on silica, eluting with 0%-50% ethyl acetate in cyclohexane. The fractions containing the desired product were concentrated under vacuum to give the title compound (86 mg). LCMS m/z 273.97 [M+H]+ R.T.=3.19 min (Analytical Method 5).

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. customthe organic solution separated
  3. washwashed with 1 N hydrochloric acid
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent evaporated
  7. customThe residue was purified by flash chromatography on silica
  8. washeluting with 0%-50% ethyl acetate in cyclohexane
  9. additionThe fractions containing the desired product
  10. concentrationwere concentrated under vacuum

Sources & evidence

ORD record
ord-7b235ee869a34a01be54e10d42f71573
Source dataset
uspto-grants-2013_12
Patent number
US08614209B2

Reaction notes

Loading…