Stannous Chloride → HCID 11396307, Verbindung

HRID 1987244

Reaktionsgleichung

Reaktionsgleichung von HRID 1987244
[NH2:1][C:2]1[CH:7]=[C:6]([CH2:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10]([N:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:11].Cl[Sn]Cl.C(C1C=CC(C(N2CCCCC2)=O)=C([N+]([O-])=O)C=1)C.Cl[S:41]([C:44]1[C:52]2[C:48](=[N:49][S:50][N:51]=2)[CH:47]=[CH:46][CH:45]=1)(=[O:43])=[O:42]>O>[CH2:8]([C:6]1[CH:5]=[CH:4][C:3]([C:10]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[O:11])=[C:2]([NH:1][S:41]([C:44]2[C:52]3=[N:51][S:50][N:49]=[C:48]3[CH:47]=[CH:46][CH:45]=2)(=[O:43])=[O:42])[CH:7]=1)[CH3:9]

Komponenten

6

Edukt 4

HCID 24479Stannous ChlorideHCID 27354592,1,3-Benzothiadiazole, 4-chlorosulfonyl-HCID 16090717(4-Ethyl-2-nitro-phenyl)-piperidin-1-yl-methanoneHCID 160907372-Amino-4-ethyl-phenyl-piperidin-1-yl-methanone

Produkt 1

HCID 11396307HCID 11396307, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-nitro-4-vinylbenzoic acid piperidine amide (100 mg, 0.39 mmol) in methanol (15 mL) was added Pd on carbon (10 wt %, 25 mg). The reaction mixture was maintained under ˜1 atm H2 and stirred for 12 h. The mixture was filtered through Celite® and concentrated in vacuo to yield (4-ethyl-2-nitro-phenyl)-piperidin-1-yl-methanone, which was subsequently reduced to (2-amino-4-ethyl-phenyl-piperidin-1-yl-methanone with SnCl2.2 H2O as described in EXAMPLE 5. The title compound was prepared from the aniline (90 mg, 0.39 mmol) and 4-chlorosulfonyl-2,1.3-benzothiadiazole (181 mg, 0.78 mmol), and purified as described in EXAMPLE 15. TLC (silica gel, 3:1 EtOAc/hexanes): Rf=0.32. MS (ESI): m/z 431 [M+H]+, 453 [M+Na]+. HPLC (reversed-phase): RT=9.52 min (single peak). 1H NMR (400 MHz, CDCl3): (rotameric broadening) 8.95 (s, 1H), 8.21 (m, 2H), 7.65 (dd, J=8.8 Hz, 7 Hz, 1H), 7.47 (d, J=1.3 Hz, 1H), 6.95 (d, J=7.8 Hz, 1H) 6.85 (dd, J=7.9 Hz, 1.6 Hz, 1H), 3.14 (bs, 4H), 2.60 (m, 2H), 1.61 (m, 2H), 1.43 (bs, 4H), 1.17 (t, J=7.6 Hz, 3H). Elemental analysis: calculated for C20H22N4O3S2, C, 55.79; H, 5.15; N, 13.01. found C, 55.44; H, 5.50; N, 12.62.

Aufarbeitung

  1. custompurified

Quellen und Nachweise

ORD-Eintrag
ord-fdb673094ec2481194d3953a6dddcfd0
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07550492B2

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