Diisopropylethylamine → HCID 59553169, Verbindung

HRID 1171422Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1171422
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH2:13][C:14]#[N:15])=[CH:4][CH:3]=1.[F:16][C:17]1[CH:18]=[C:19]([CH:23]=[C:24]([N:26]2[CH2:31][CH2:30][CH:29]([CH3:32])[CH2:28][CH2:27]2)[CH:25]=1)[C:20](O)=[O:21].C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C)C=O.C(OCC)(=O)C>[C:14]([CH2:13][O:12][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([NH:1][C:20](=[O:21])[C:19]2[CH:23]=[C:24]([N:26]3[CH2:27][CH2:28][CH:29]([CH3:32])[CH2:30][CH2:31]3)[CH:25]=[C:17]([F:16])[CH:18]=2)=[CH:3][CH:4]=1)#[N:15]

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59553077(4-Aminonaphthalen-1-yloxy)-acetonitrileHCID 595533113-Fluoro-5-(4-methylpiperidin-1-yl)benzoic acid

Produkt 1

HCID 59553169HCID 59553169, VerbindungAusbeute 13,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

(4-Aminonaphthalen-1-yloxy)-acetonitrile (1.068 g, 5.4 mmol), 3-fluoro-5-(4-methylpiperidin-1-yl)-benzoic acid (1.27 g, 5.4 mmol), diisopropylethylamine (3 ml) and HBTU (2.45 g, 6.5 mmol) are stirred at room temperature in anhydrous dimethylformamide (20 ml) for 1 day. The mixture is then poured into ethyl acetate (200 ml) and washed with water (2×200 ml). The organic layer is then dried over anhydrous sodium sulfate and evaporated to dryness. The residue is purified by column chromatography on silica gel eluted with 25-30% ethyl acetate in hexanes to give a pale purple solid. This is then recrystallized from ethyl acetate/methanol to give N-(4-cyanomethoxynaphthalen-1-yl)-3-fluoro-5-(4-methylpiperidin-1-yl)-benzamide as a pale purple solid (303 mg). 1H NMR 300 MHz (CDCl3) 8.27 (d, 1H, J=7.5 Hz), 7.94 (s, 1H), 7.86 (t, 2H, J=9.6 Hz), 7.6 (m, 2H), 7.3 (s, 1H), 6.97 (m, 2H), 6.77 (d, 1H, J=11.4 Hz), 5.0 (s, 1H), 3.77 (m, 2H), 2.83 (m, 2H), 1.75 (m, 2H), 1.25-1.4 (m, 3H), 1.0 (d, 3H).

Aufarbeitung

  1. washwashed with water (2×200 ml)
  2. dry with materialThe organic layer is then dried over anhydrous sodium sulfate
  3. customevaporated to dryness
  4. customThe residue is purified by column chromatography on silica gel
  5. washeluted with 25-30% ethyl acetate in hexanes
  6. customto give a pale purple solid
  7. customThis is then recrystallized from ethyl acetate/methanol

Quellen und Nachweise

ORD-Eintrag
ord-b07e096f38cf404ebb20f0f3115288c4
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07829560B2

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