4-Piperidinecarboxylic acid → HCID 10142564, compound

HRID 1246868Notes

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[CH2:42][CH2:41][CH:37]([C:38]([OH:40])=[O:39])[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[CH2:42][CH2:41][CH:37]([C:38]([OH:40])=[O:39])[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

Reactant 3

HCID 37734-Piperidinecarboxylic acid

HCID 982104-Hydroxypyrrolidine

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

Product 1

HCID 10142564HCID 10142564, 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 isonipecotic acid. A yellow solid 127 was obtained (0.014 g, 28%). 1H-NMR (CDCl3, 400 MHz) δ 1.89–1.98 (m, 2H), 2.08–2.15 (m, 2H), 2.68–2.76 (m, 1H), 3.40–3.48 (m, 2H), 4.13–4.20 (m, 2H), 4.28–4.34 (m, 4H), 6.91–6.98 (m, 3H), 7.04 (dd, J=1.9 Hz, 8.4 Hz, 1H), 7.09 (d, J=2.2 Hz, 1H), 7.12 (d, J=8.4 Hz, 1H), 7.52 (d, J=8.4 Hz, 1H), 7.82 (s, 1H), 8.20 (d, J=6.2 Hz, 1H); MS (APCI) m/z 517 (M+H)+.

Sources & evidence

ORD record: ord-c032415293464084a33e7f52091cfb6e
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07129247B2

Reaction notes

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