Diisopropylethylamine → HCID 11949731, Verbindung

HRID 1766509Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1766509
[CH:1]1([CH2:4][O:5][C:6]2[C:14]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)=[CH:13][C:9]([C:10]([OH:12])=O)=[CH:8][N:7]=2)[CH2:3][CH2:2]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)C(C)C)(C)C.[NH2:53][CH2:54][C@H:55]1[CH2:60][CH2:59][CH2:58][CH2:57][C@H:56]1[OH:61]>CN(C=O)C>[CH:1]1([CH2:4][O:5][C:6]2[C:14]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)=[CH:13][C:9]([C:10]([NH:53][CH2:54][C@@H:55]3[CH2:60][CH2:59][CH2:58][CH2:57][C@@H:56]3[OH:61])=[O:12])=[CH:8][N:7]=2)[CH2:2][CH2:3]1

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 12483365cis-2-Aminomethyl-1-cyclohexanolHCID 211097215-(4-Fluorophenyl)-6-cyclopropylmethoxy-nicotinic acid

Produkt 1

HCID 11949731HCID 11949731, VerbindungAusbeute 73,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

6-Cyclopropylmethoxy-5-(4-fluoro-phenyl)-nicotinic acid (0.50 g, 2 mmol) was dissolved in DMF (20 mL). To the solution was added TBTU (0.62 g, 2 mmol), N,N-diisopropylethyl amine (1.5 mL, 9 mmol) and cis-2-aminomethyl-1-cyclohexanol (317 mg, 2 mmol). The reaction mixture was stirred for 18 h at room temperature. The solvent was evaporated in vacuo and the residue was purified by column chromatography on silica (n-heptane/ethyl acetate gradient) to yield 585 mg of the title compound as a colorless solid, MS (ISP) 399.2 (M+H)+.

Aufarbeitung

  1. customThe solvent was evaporated in vacuo
  2. customthe residue was purified by column chromatography on silica (n-heptane/ethyl acetate gradient)

Quellen und Nachweise

ORD-Eintrag
ord-61f020651ff843e19a7d1e6e24d4289e
Quelldatensatz
uspto-grants-2007_06
Patentnummer
US07229999B2

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