Dibutylamine → HCID 86718950, compound

HRID 529033Notes

Reaction equation

HRID 529033 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=O)[CH:5]=[CH:4][CH:3]=1.[CH2:11]([NH:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:12][CH2:13][CH3:14].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[Br:1][C:2]1[N:7]=[C:6]([C:8]([N:15]([CH2:16][CH2:17][CH2:18][CH3:19])[CH2:11][CH2:12][CH2:13][CH3:14])=[O:10])[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8148DibutylamineHCID 81531DiisopropylethylamineHCID 5939196-Bromopyridine-2-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 86718950HCID 86718950, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-bromopicolinic acid (Aldrich, 404 mg, 2.00 mmol) in DMF (3.0 mL) were added dibutylamine (Aldrich, 258 mg, 2.00 mmol), HATU (760 mg, 2.00 mmol) and DIEA (1.1 mL, 6.00 mmol). The reaction mixture was stirred at room temperature for 3 h and then quenched by adding sat. aq. NH4Cl solution. The mixture was extracted with EtOAc (3×). The combined organic extracts were dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash column chromatography, gradient from 0 to 20% EtOAc/DCM to give a light brown oil (450 mg, 72%). 1H NMR (CDCl3) δ 7.67-7.57 (m, 2H), 7.51 (dd, J=7.5, 1.3 Hz, 1H), 3.53-3.42 (m, 2H), 3.36-3.27 (m, 2H), 1.72-1.56 (m, 4H), 1.46-1.33 (m, 2H), 1.27-1.15 (m, 2H), 0.97 (t, J=7.4 Hz, 3H), 0.85 (t, J=7.4 Hz, 3H); MS(ESI+) m/z 313.2 (M+H)+.

Workup

  1. customquenched
  2. additionby adding sat. aq. NH4Cl solution
  3. extractionThe mixture was extracted with EtOAc (3×)
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography, gradient from 0 to 20% EtOAc/DCM

Sources & evidence

ORD record
ord-65cda412c3d440eeb1cb8b10a283f71d
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

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