Diisopropylethylamine → 5-Bromo-N-(2-cyclopropyl-2-hydroxy-propyl)-6-(2,2,2-trifluoro-ethoxy)-2-trifluoromethyl-nicotinamide

HRID 598228Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 598228
[Br:1][C:2]1[C:3]([O:15][CH2:16][C:17]([F:20])([F:19])[F:18])=[N:4][C:5]([C:11]([F:14])([F:13])[F:12])=[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.[NH2:52][CH2:53][C:54]([CH3:59])([CH:56]1[CH2:58][CH2:57]1)[OH:55]>CN(C=O)C>[Br:1][C:2]1[C:3]([O:15][CH2:16][C:17]([F:20])([F:19])[F:18])=[N:4][C:5]([C:11]([F:14])([F:13])[F:12])=[C:6]([CH:10]=1)[C:7]([NH:52][CH2:53][C:54]([CH:56]1[CH2:58][CH2:57]1)([OH:55])[CH3:59])=[O:9]

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 211096921-Amino-2-cyclopropylpropan-2-olHCID 863463205-Bromo-6-(2,2,2-trifluoroethoxy)-2-(trifluoromethyl)nicotinic acid

Produkt 1

HCID 866347985-Bromo-N-(2-cyclopropyl-2-hydroxy-propyl)-6-(2,2,2-trifluoro-ethoxy)-2-trifluoromethyl-nicotinamideAusbeute 27,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

5-Bromo-6-(2,2,2-trifluoro-ethoxy)-2-trifluoromethyl-nicotinic acid (1.1 g, 3.0 mmol) was dissolved in DMF (25 mL). To the solution was added TBTU (1.06 g, 3.3 mmol), N,N-diisopropylethyl amine (2.54 mL, 15 mmol) and α-(aminomethyl)-α-methyl-cyclopropanemethanol (0.38 g, 3.3 mmol). The reaction mixture was stirred for 16 h at room temperature. The solvent was evaporated in vacuo and the residue dissolved in ethyl acetate (20 mL), washed with sodium hydroxide solution (0.5 N) and brine. Organic phases were pooled, dried with MgSO4 and concentrated in vacuo. The residue was purified by flash chromatography (SiO2, heptane/ethyl acetate) to give the title compound (0.38 g) as a light yellow solid, MS (ISP) 462.9, 464.9 (M−H)+.

Aufarbeitung

  1. customThe solvent was evaporated in vacuo
  2. dissolutionthe residue dissolved in ethyl acetate (20 mL)
  3. washwashed with sodium hydroxide solution (0.5 N) and brine
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography (SiO2, heptane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-6402f0a619344f398036353ce5c2073e
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07897621B2

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