Piperidin-4-ol → 4'-(4-(2,3-Dihydro-benzo(1,4)dioxin-6-ylsulfanyl)-3-trifluoromethyl-phenyl)-3,4,5,6-tetrahydro-2H-(1,2')bipyridinyl-4-ol

HRID 1005821Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1005821
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([S:11][C:12]3[CH:17]=[CH:16][C:15]([C:18]4[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=4)=[CH:14][C:13]=3[C:24]([F:27])([F:26])[F:25])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.OC1CCNC1.[OH:34][CH:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1>>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([S:11][C:12]3[CH:17]=[CH:16][C:15]([C:18]4[CH:19]=[CH:20][N:21]=[C:22]([N:38]5[CH2:39][CH2:40][CH:35]([OH:34])[CH2:36][CH2:37]5)[CH:23]=4)=[CH:14][C:13]=3[C:24]([F:25])([F:26])[F:27])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Komponenten

4

Edukt 3

HCID 79341Piperidin-4-olHCID 982104-HydroxypyrrolidineHCID 865858674-(4-(2,3-Dihydro-benzo(1,4)dioxin-6-ylsulfanyl)-3-trifluoromethyl-phenyl)-pyridine

Produkt 1

HCID 219067944'-(4-(2,3-Dihydro-benzo(1,4)dioxin-6-ylsulfanyl)-3-trifluoromethyl-phenyl)-3,4,5,6-tetrahydro-2H-(1,2')bipyridinyl-4-ol

Versuchsvorschrift

The title compound was prepared according to the procedures of Example 38E, substituting compound 76 with compound 118 (0.033 g, 0.0779 mmol) and 3-hydroxypyrrolidine with 4-hydroxypiperdine. A yellow solid 119 was obtained (0.031 g, 63%). 1H-NMR (CDCl3, 400 MHz) δ 1.75-1.84 (m, 2H), 2.02-2.10 (m, 2H), 3.67-3.74 (m, 2H), 4.00-4.07 (m, 2H), 4.10-4.16 (m, 1H), 4.28-4.34 (m, 4H), 4.72-4.76 (m, 1H), 6.93-6.97 (m, 3H), 7.05 (dd, J=1.8 Hz, 8.0 Hz, 1H), 7.10 (d, J=1.8 Hz, 1H), 7.12 D, J=8.5 Hz, 1H), 7.52 (d, J=8.4 Hz, 1H), 7.82 (s, 1H), 8.25 (d, J=6.3 Hz, 1H), MS (APCI) m/z 489 (M+H)+.

Quellen und Nachweise

ORD-Eintrag
ord-10c1712289a6438f942b30b97ee25c44
Quelldatensatz
uspto-grants-2004_09
Patentnummer
US06787542B2

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