4-Hydroxypyrrolidine → HCID 21906782, compound

HRID 1246875Notes

Reaction equation

HRID 1246875 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.[CH2:34]([N:37]1[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1)[CH2:35][CH3:36]>>[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]([CH2:34][CH2:35][CH3:36])[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 982104-HydroxypyrrolidineHCID 415812Piperazine, 1-propyl-, hydrochloride (1:2)HCID 865858674-(4-(2,3-Dihydro-benzo(1,4)dioxin-6-ylsulfanyl)-3-trifluoromethyl-phenyl)-pyridine

Product 1

HCID 21906782HCID 21906782, 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 1-propylpiperazine. A yellow solid 135 was obtained (0.033 g, 64%). 1H-NMR (CDCl3, 400 MHz) δ 1.03 (t, J=7.3 Hz, 3H), 1.84–1.92 (m, 2H), 2.30–2.52 (br, 8H), 2.98–3.03 (m, 2H), 4.28–4.34 (m, 4H), 6.87 (s, 1H), 6.94 (d, J=8.1 Hz, 1H), 7.01 (d, J=5.8 Hz, 1H), 7.04 (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), 7.51 (d, J=8.3 Hz, 1H), 7.82 (s, 1H), 8.26 (d, J=5.9 Hz, 1H); MS (APCI) m/z 516 (M+H)+.

Sources & evidence

ORD record
ord-a0afe286281c4a358baf478e11406382
Source dataset
uspto-grants-2006_10
Patent number
US07129247B2

Reaction notes

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