Diisopropylethylamine → HCID 66775665, compound

HRID 1645445Notes

Reaction equation

HRID 1645445 reaction equation
[CH:1]([O:4][C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[CH:7][CH:6]=1)([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.[O:45]=[C:46]1[CH2:51][CH2:50][CH2:49][CH:48]([C:52](O)=[O:53])[CH2:47]1>C(OCC)(=O)C.CN(C=O)C>[CH:1]([O:4][C:5]1[CH:11]=[CH:10][C:8]([NH:9][C:52]([CH:48]2[CH2:49][CH2:50][CH2:51][C:46](=[O:45])[CH2:47]2)=[O:53])=[CH:7][CH:6]=1)([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 821124-IsopropoxyanilineHCID 27602523-Oxocyclohexane-1-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 66775665HCID 66775665, compoundYield 100.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Isopropoxyaniline (117 mg, 0.774 mmol), HATU (294 mg, 0.774 mmol) and diisopropylethylamine (0.27 mL, 1.548 mmol) were added in that order to a DMF (3 mL) solution of 3-oxo-1-cyclohexanecarboxylic acid (100 mg, 0.703 mmol), and stirred at room temperature for 5 hours. Ethyl acetate was added to the reaction liquid, and washed with distilled water and saturated brine. The organic layer was dried with magnesium sulfate, and concentrated under reduced pressure. The residue was purified through silica gel column chromatography to give the intended product (194 mg, 100%).

Workup

  1. washwashed with distilled water and saturated brine
  2. dry with materialThe organic layer was dried with magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-1d0a3014b6c54bbc811b2296079caeba
Source dataset
uspto-grants-2012_02
Patent number
US08124807B2

Reaction notes

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