Triethylamine → HCID 59542541, compound

HRID 1809103Notes

Reaction equation

HRID 1809103 reaction equation
[Br:1][C:2]1[S:6][CH:5]=[C:4]([C:7]([OH:9])=O)[CH:3]=1.C(N(CC)CC)C.[CH3:17][C:18]1([CH3:24])[CH2:23][CH2:22][CH2:21][NH:20][CH2:19]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(#N)C>[Br:1][C:2]1[S:6][CH:5]=[C:4]([C:7]([N:20]2[CH2:21][CH2:22][CH2:23][C:18]([CH3:24])([CH3:17])[CH2:19]2)=[O:9])[CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 709423,3-DimethylpiperidineHCID 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 59542541HCID 59542541, compoundYield 65.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5-Bromothiophene-3-carboxylic acid (0.5 g, 2.4 mmol) was dissolved in acetonitrile (10 mL) and triethylamine (7.1 mmol). 3,3-Dimethylpiperidine (2.4 mmol) and HATU (2.4 mmol) were added and the reaction stirred at room temperature overnight. The solvent was evaporated and the residue dissolved in DCM and washed with water. After drying with anhydrous magnesium sulphate, the solution was filtered and evaporated and the residue purified by flash chromatography on silica, eluting with 0-40% ethyl acetate in cyclohexane. The fractions containing the desired product were combined and evaporated to give the title compound as a white crystalline solid (0.475 g). 1H NMR δ (ppm)(CHCl3-d): 7.4 (s, 1H), 7.1 (s, 1H), 3.6-3.1 (m, 4H), 1.7 (m, 2H), 1.4 (m, 2H), 0.9 (s, 6H).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue dissolved in DCM
  3. washwashed with water
  4. dry with materialAfter drying with anhydrous magnesium sulphate
  5. filtrationthe solution was filtered
  6. customevaporated
  7. customthe residue purified by flash chromatography on silica
  8. washeluting with 0-40% ethyl acetate in cyclohexane
  9. additionThe fractions containing the desired product
  10. customevaporated

Sources & evidence

ORD record
ord-773459dee9d14f79841684e9ae57dc0c
Source dataset
uspto-grants-2013_01
Patent number
US08362008B2

Reaction notes

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