1-Acetylpiperazine → 1-(4-(4-(4-(2,3-Dihydro-benzo(1,4)dioxin-6-ylsulfanyl)-3-trifluoromethyl-phenyl)-pyridin-2-yl)-piperazin-1-yl)-ethanone

HRID 1246866Notes

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.[C:34]([N:37]1[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1)(=[O:36])[CH3:35]>>[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][N:37]([C:34](=[O:36])[CH3:35])[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

Reactant 3

HCID 837951-Acetylpiperazine

HCID 982104-Hydroxypyrrolidine

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

Product 1

HCID 219067671-(4-(4-(4-(2,3-Dihydro-benzo(1,4)dioxin-6-ylsulfanyl)-3-trifluoromethyl-phenyl)-pyridin-2-yl)-piperazin-1-yl)-ethanone

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 1-acetylpiperazine. A yellow solid 125 was obtained (0.010 g, 19%). 1H-NMR (CDCl3, 400 MHz) δ 2.17 (s, 3H), 3.67–3.72 (m, 2H), 3.73–3.77 (m, 2H), 3.83–3.88 (m, 2H), 3.94–3.98 (m, 2H), 4.28–4.34 (m, 4H), 6.93 (s, 1H), 6.95 (d, J=8.4 Hz, 1H), 7.02 (d, J=5.8 Hz, 1H), 7.05 (dd, J=2.2 Hz, 8.4 Hz, 1H), 7.09 (d, J=2.2 Hz, 1H), 7.13 (d, J=8.4 Hz, 1H), 7.53 (d, J=8.1 Hz, 1H), 7.83 (s, 1H), 8.29 (d, J=6.2 Hz, 1H); MS (APCI) m/z 516 (M+H)+.

Sources & evidence

ORD record: ord-09ff9f1321bf4f3e98e63311e41c1361
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07129247B2

Reaction notes

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