Diisopropylethylamine → HCID 69812169, compound

HRID 1516379Notes

Reaction equation

HRID 1516379 reaction equation
[Br:1][C:2]1[C:3]([O:11][CH2:12][C:13]([F:16])([F:15])[F:14])=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)C(C)C)(C)C.[NH2:48][C@@H:49]1[CH2:54][CH2:53][CH2:52][CH2:51][C@H:50]1[OH:55]>CN(C=O)C>[Br:1][C:2]1[C:3]([O:11][CH2:12][C:13]([F:16])([F:15])[F:14])=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([NH:48][C@@H:49]1[CH2:54][CH2:53][CH2:52][CH2:51][C@H:50]1[OH:55])=[O:9]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 735777(1R,2R)-2-AminocyclohexanolHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 581925925-Bromo-6-(2,2,2-trifluoroethoxy)-3-pyridinecarboxylic acid

Product 1

HCID 69812169HCID 69812169, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Bromo-6-(2,2,2-trifluoro-ethoxy)-nicotinic acid (50.0 g, 0.166 mol) was dissolved in DMF (600 mL). To the solution was added TBTU (58.9 g, 0.183 mol), N,N-diisopropylethyl amine (142.6 mL, 0.83 mol) and (1R,2R)-2-amino-cyclohexanol (21.1 g, 0.183 mol). The reaction mixture was stirred for 3 h at room temperature. The solvent was evaporated in vacuo, the residue was dissolved in a mixture of ethyl acetate (1200 mL) and THF (300 mL). The solution was washed twice with water (700 mL) and the water phases were extracted with ethyl acetate (600 mL). Organic phases were pooled, dried with MgSO4 and concentrated to about 900 mL. The product precipitated upon stirring and cooling to 0° C. Filtration, washing with ethyl acetate/n-heptane (1:1) and drying in vacuo gave the title compound (53.1 g) as a white solid; MS (ISP) 397, 399 (M)+.

Workup

  1. customThe solvent was evaporated in vacuo
  2. dissolutionthe residue was dissolved in a mixture of ethyl acetate (1200 mL) and THF (300 mL)
  3. washThe solution was washed twice with water (700 mL)
  4. extractionthe water phases were extracted with ethyl acetate (600 mL)
  5. dry with materialdried with MgSO4
  6. concentrationconcentrated to about 900 mL
  7. customThe product precipitated
  8. stirringupon stirring
  9. temperaturecooling to 0° C
  10. filtrationFiltration
  11. washwashing with ethyl acetate/n-heptane (1:1)
  12. customdrying in vacuo

Sources & evidence

ORD record
ord-f913c72462294a90bfb04f459cc32648
Source dataset
uspto-grants-2012_07
Patent number
US08227491B2

Reaction notes

Loading…