N-Methylpropylamine → Methyl 3-iodo-5-{[methyl(propyl)amino]carbonyl}benzoate

HRID 14065

Reaktionsgleichung

Reaktionsgleichung von HRID 14065
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[CH:10]=1)[C:5]([OH:7])=O.C(N(C(C)C)CC)(C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)[C:35]2[N:36]=[CH:37]C=[CH:39][C:34]=2N=N1.CNCCC>CN(C=O)C.C(OCC)(=O)C>[I:1][C:2]1[CH:10]=[C:9]([CH:8]=[C:4]([C:5]([N:36]([CH3:37])[CH2:35][CH2:34][CH3:39])=[O:7])[CH:3]=1)[C:11]([O:13][CH3:14])=[O:12]

Komponenten

7

Edukt 4

HCID 12315N-MethylpropylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 158403913-Iodo-5-(methoxycarbonyl)benzoic acid

Produkt 1

HCID 21086185Methyl 3-iodo-5-{[methyl(propyl)amino]carbonyl}benzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To 3-iodo-5-(methoxycarbonyl)benzoic acid (1.0 g, 3.3 mmol), prepared as in Example SP-281, step 1, and diisopropylethylamine (1.7 mL, 9.8 mmol) in DMF (10 mL) is added O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU, 1.5 g, 3.9 mmol) then N-methylpropylamine (503 μL, 4.9 mmol). The solution is stirred at room temperature 2 h. The solution is diluted in ethyl acetate and washed with water, saturated sodium bicarbonate, and brine. The organic layer is dried over sodium sulfate, filtered and concentrated under reduced pressure to give the title compound in crude form. This material is purified by flash chromatography (40% ethyl acetate/hexane) to give the purified title compound. MS (ESI) [M+H+]=362.4.

Aufarbeitung

  1. washwashed with water, saturated sodium bicarbonate, and brine
  2. dry with materialThe organic layer is dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-06f535eff89946a9aca5b9bdbe30e5b5
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07727997B2

Verknüpfte Notizen

Wird geladen…