N-[6-(2-phenylchroman-6-yloxy)pyridin-3-yl]methanesulfonamide → N-{6-[2-(4-Fluorophenyl)chroman-6-yloxy]pyridin-3-yl}methane sulfonamide

HRID 31295

Reaktionsgleichung

Reaktionsgleichung von HRID 31295
[C:1]1([CH:7]2[CH2:16][CH2:15][C:14]3[C:9](=[CH:10][CH:11]=[C:12]([O:17][C:18]4[N:23]=[CH:22][C:21]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])=[CH:20][CH:19]=4)[CH:13]=3)[O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:29]C1C=CC(C2CCC3C(=CC=C(OC4N=CC(N)=CC=4)C=3)O2)=CC=1>C(OCC)(=O)C.CCCCCCC>[F:29][C:4]1[CH:5]=[CH:6][C:1]([CH:7]2[CH2:16][CH2:15][C:14]3[C:9](=[CH:10][CH:11]=[C:12]([O:17][C:18]4[N:23]=[CH:22][C:21]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])=[CH:20][CH:19]=4)[CH:13]=3)[O:8]2)=[CH:2][CH:3]=1

Komponenten

4

Edukt 2

HCID 17978472N-[6-(2-phenylchroman-6-yloxy)pyridin-3-yl]methanesulfonamideHCID 179785666-[2-(4-Fluorophenyl)chroman-6-yloxy]pyridin-3-ylamine

Produkt 1

HCID 17978608N-{6-[2-(4-Fluorophenyl)chroman-6-yloxy]pyridin-3-yl}methane sulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21899848Ethylacetate heptaneLösungsmittel

Versuchsvorschrift

N-{6-[2-(4-Fluorophenyl)chroman-6-yloxy]pyridin-3-yl}methane sulfonamide was prepared as described for N-[6-(2-phenylchroman-6-yloxy)pyridin-3-yl] methane sulfonamide in Example 46 starting from 442 mg of 6-[2-(4-fluorophenyl)-chroman-6-yloxy]-pyridin-3-ylamine (Example 76). The product was passed through silica gel using ethyl acetate-heptane (10:3) as an eluant and then crystallised from diethyl ether. 1H NMR (400 MHz, CDCl3) δ: 8.09 (d, 1H, J 2.8 Hz), 7.72 (dd, 1H, J 8.9, 2.8 Hz), 7.40 (m, 2H), 7.08 (m, 2H), 6.92-6.87 (m, 4H), 6.74 (s, 1H), 5.03 (dd, 1H, J 10.4, 2.3 Hz), 3.01 (m, 1H), 3.00 (s, 3H), 2.80 (m, 1H), 2.19 (m, 1H), 2.07 (m, 1H).

Aufarbeitung

  1. customcrystallised from diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-5ff2e3f6a2534af2b608d0b3dcc8ae6f
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425568B2

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