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

HRID 1005824Notes

Reaction equation

HRID 1005824 reaction equation
[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.[NH:34]1[CH2:39][CH2:38][CH:37]([CH2:40][OH:41])[CH2:36][CH2:35]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:34]5[CH2:39][CH2:38][CH:37]([CH2:40][OH:41])[CH2:36][CH2:35]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

Participants

4

Reactant 3

HCID 982104-HydroxypyrrolidineHCID 4207714-PiperidinemethanolHCID 865858674-(4-(2,3-Dihydro-benzo(1,4)dioxin-6-ylsulfanyl)-3-trifluoromethyl-phenyl)-pyridine

Product 1

HCID 21906802(4'-(4-(2,3-Dihydro-benzo(1,4)dioxin-6-ylsulfanyl)-3-trifluoromethyl-phenyl)-3,4,5,6-tetrahydro-2H-(1,2')bipyridinyl-4-yl)-methanol

Procedure

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-piperidinemethanol. A yellow solid 122 was obtained (0.0284 g, 57%). 1H-NMR (CDCl3, 400 MHz) δ 1.41-1.51 (m, 2H), 1.86-1.95 (m, 1H), 1.97-2.04 (m, 2H), 3.23-3.31 (m, 2H), 3.57 (d, J=5.8 Hz, 2H), 4.28-4.34 (m, 4H), 4.36-4.41 (m, 2H), 6.92 (d, J=6.6 Hz, 1H), 6.93-6.97 (m, 2H), 7.05 (dd, J=1.8 Hz, 8.4 Hz, 1H),7.09 (d, J=1.8 Hz, 1H), 7.12 (d, J=8.4 Hz, 1H), 7.52 (d, J=8.4 Hz, 1H), 7.82 (s, 1H), 8.25 (d, J=6.6 Hz, 1H); MS (APCI) m/z 503 (M+H)+.

Sources & evidence

ORD record
ord-8ac6308d3f034f149e47518606ca9297
Source dataset
uspto-grants-2004_09
Patent number
US06787542B2

Reaction notes

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