Triethylamine → HCID 117840323, compound

HRID 714863Notes

Reaction equation

HRID 714863 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2([C:16]([OH:18])=O)[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl.CN.[CH2:22]([N:24](CC)CC)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C)C(=O)C.O1CCCC1>[CH3:22][NH:24][C:16]([C:10]1([C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1)=[O:18]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 6364545Methylamine hydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58994943HCID 58994943, compound

Product 1

HCID 117840323HCID 117840323, compoundYield 50.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 31374DimethylacetamideSolvent

Procedure

To a solution of 4-(4-nitrophenyl)tetrahydro-2H-pyran-4-carboxylic acid (750 mg) obtained in Step B of Example 151, methanamine hydrochloride (1.0 g) and triethylamine (3.0 g) in a mixed solvent of tetrahydrofuran (20 mL) and N,N-dimethylacetamide (5.0 mL) was added 2-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (0.86 g), and the mixture was stirred at room temperature for 10 hr. The solvent was evaporated under reduced pressure, and the reaction mixture was poured into water, and extracted with ethyl acetate. The obtained organic layer was washed with saturated aqueous sodium hydrogen carbonate solution, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate) to give the title compound (400 mg).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionthe reaction mixture was poured into water
  3. extractionextracted with ethyl acetate
  4. washThe obtained organic layer was washed with saturated aqueous sodium hydrogen carbonate solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate)

Sources & evidence

ORD record
ord-72405fd7b85a4589bcaf06e9587492a9
Source dataset
uspto-grants-2015_11
Patent number
US09187453B2

Reaction notes

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