Cyclopropylamine → 5-Hydroxymethyl-pyridine-2-carboxylic acid cyclopropylamide

HRID 851969Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 851969
[OH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]([OH:11])=O)=[N:7][CH:8]=1.[B-](F)(F)(F)F.CN(C(O[N:25]1[C:30](=O)[CH:29]=[CH:28]C=C1)=[N+](C)C)C.CCN(C(C)C)C(C)C.C1(N)CC1>CN(C=O)C>[CH:30]1([NH:25][C:9]([C:6]2[CH:5]=[CH:4][C:3]([CH2:2][OH:1])=[CH:8][N:7]=2)=[O:11])[CH2:28][CH2:29]1

Komponenten

6

Edukt 4

HCID 69828CyclopropylamineHCID 81531DiisopropylethylamineHCID 2733204O-(2-Oxo-1(2H)-pyridyl)-N,N,N',N'-tetramethyluronium TetrafluoroborateHCID 135185635-(Hydroxymethyl)pyridine-2-carboxylic acid

Produkt 1

HCID 694914535-Hydroxymethyl-pyridine-2-carboxylic acid cyclopropylamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

5-Hydroxymethyl-pyridine-2-carboxylic acid (0.23 g, 1.5 mmol) was dissolved in DMF (3 ml) and activated with TPTU (0.45 g, 1.5 mmol), Hünig's base (0.51 ml, 3.0 mmol) and reacted with cyclopropyl amine (0.12 ml, 1.65 mmol) for 1 h at r.t during which a precipitate was formed. Solvent was removed and the residue dissolved in acetonitrile/water and purified by prep.RP(C18)HPLC: 60 mg;

Aufarbeitung

  1. customwas formed
  2. customSolvent was removed
  3. dissolutionthe residue dissolved in acetonitrile/water
  4. custompurified by prep.RP(C18)HPLC: 60 mg

Quellen und Nachweise

ORD-Eintrag
ord-ecb1f1d616ea4181beade1ca658b9927
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07253158B2

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