Methanol → 3-fluoro-5-(4-methylpiperidin-1-yl)-N-[4-(2H-tetrazol-5-ylmethoxy)-naphthalen-1-yl]-benzamide

HRID 1641291Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1641291
[C:1]([CH2:3][O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([NH:15][C:16](=[O:31])[C:17]2[CH:22]=[C:21]([N:23]3[CH2:28][CH2:27][CH:26]([CH3:29])[CH2:25][CH2:24]3)[CH:20]=[C:19]([F:30])[CH:18]=2)=[CH:7][CH:6]=1)#[N:2].C[Si]([N:36]=[N+:37]=[N-:38])(C)C.C([Sn](=O)CCCC)CCC.CO>C1(C)C=CC=CC=1>[F:30][C:19]1[CH:18]=[C:17]([CH:22]=[C:21]([N:23]2[CH2:24][CH2:25][CH:26]([CH3:29])[CH2:27][CH2:28]2)[CH:20]=1)[C:16]([NH:15][C:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:5]([O:4][CH2:3][C:1]2[N:36]=[N:37][NH:38][N:2]=2)=[CH:6][CH:7]=1)=[O:31]

Komponenten

6

Edukt 4

HCID 887MethanolHCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 59553169HCID 59553169, Verbindung

Produkt 1

HCID 595530853-fluoro-5-(4-methylpiperidin-1-yl)-N-[4-(2H-tetrazol-5-ylmethoxy)-naphthalen-1-yl]-benzamideAusbeute 0 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

N-(4-Cyanomethoxynaphthalen-1-yl)-3-fluoro-5-(4-methylpiperidin-1-yl)-benzamide (54 mg, 129 mmol), trimethylsilylazide (0.1 ml, 760 mmol) and dibutyltin oxide (5 mg) are heated to reflux in anhydrous toluene (3 ml) for 5 hours. After cooling to room temperature methanol (5 ml) is then added and the mixture stirred at room temperature for 30 min. The mixture is then evaporated to dryness and the residue recrystalized from ethyl acetate/hexanes to give 3-fluoro-5-(4-methylpiperidin-1-yl)-N-[4-(2H-tetrazol-5-ylmethoxy)-naphthalen-1-yl]-benzamide as a grey powder (22 mg). 1H NMR 300 MHz (DMSO-d6) 10.3(s, 1H), 8.32(dd, 1H, J=8.7 and 2.7 Hz), 7.87(d, 1H, J=9.3 Hz), 7.54-7.62(m, 2H), 7.42-7.5(m, 2H), 7.17(dd, 1H, J=15.9 and 9.3 Hz), 6.97(d, 1H, J=13.2 Hz), 5.7(s, 2H), 3.85(d, 2H, J=19.8 Hz), 2.77(m, 2H), 1.5-1.78(m, 3H), 1.25(m, 2H), 0.95(d, 3H, J=6.6 Hz).

Aufarbeitung

  1. additionis then added
  2. customThe mixture is then evaporated to dryness
  3. customthe residue recrystalized from ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-7a7d23be24924ca6a1eb5ecd3f7f5227
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08114873B2

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