4-Piperidineethanol → HCID 21906760, compound

HRID 1005831Notes

Reaction equation

HRID 1005831 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.[OH:34][CH2:35][CH2:36][CH:37]1[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]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:40]5[CH2:41][CH2:42][CH:37]([CH2:36][CH2:35][OH:34])[CH2:38][CH2:39]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 739534-PiperidineethanolHCID 982104-HydroxypyrrolidineHCID 865858674-(4-(2,3-Dihydro-benzo(1,4)dioxin-6-ylsulfanyl)-3-trifluoromethyl-phenyl)-pyridine

Product 1

HCID 21906760HCID 21906760, compound

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-(2′-hydroxyethyl)piperidine. A yellow solid 129 was obtained (0.037 g, 73%). 1H NMR (CDCl3, 400 MHz) δ 1.35-1.44 (m, 2H), 1.55-1.60 (m, 2H), 1.84-1.93 (m, 1H), 1.97-2.03 (m, 2H), 3.22-3.30 (m, 2H), 3.74 (t, J=6.2 Hz, 2H), 4.28-4.34 (m, 4H), 4.36-4.42 (m, 2H), 6.91 (d, J=6.6 Hz, 1H), 6.93-6.96 (m, 2H), 7.05 (dd, J=2.2 Hz, 8.4 Hz, 1H), 7.09 (d, J=2.2 Hz, 1H), 7.12 (d, J=8.8 Hz, 1H), 7.51 (d, J=8.8 Hz, 1H), 7.81 (s, 1H), 8.24 (d, J=6.6 Hz, 1H); MS (APCI) m/z 517 (M+H)+.

Sources & evidence

ORD record
ord-fb328fc10dbe4560954aef1f7be8719b
Source dataset
uspto-grants-2004_09
Patent number
US06787542B2

Reaction notes

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