4-Hydroxypyrrolidine → HCID 21906810, compound

HRID 1246876Notes

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)[CH:35]=[CH2:36]>>[CH2:34]([N:37]1[CH2:42][CH2:41][N:40]([C:22]2[CH:23]=[C:18]([C:15]3[CH:16]=[CH:17][C:12]([S:11][C:9]4[CH:8]=[CH:7][C:6]5[O:1][CH2:2][CH2:3][O:4][C:5]=5[CH:10]=4)=[C:13]([C:24]([F:25])([F:26])[F:27])[CH:14]=3)[CH:19]=[CH:20][N:21]=2)[CH2:39][CH2:38]1)[CH:35]=[CH2:36]

Participants

Reactant 3

HCID 982104-Hydroxypyrrolidine

HCID 8064221-Allylpiperazine

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

Product 1

HCID 21906810HCID 21906810, 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-allylpiperazine. A yellow solid 136 was obtained (0.037 g, 73%). 1H-NMR (CDCl3, 400 MHz) δ 2.10–2.55 (br m, 6H), 3.24–3.45 (br m, 2H), 3.7 (d, J=7.0 Hz, 2H), 4.06–4.20 (br, 2H), 4.28–4.34 (m, 4H), 5.54 (d, J=7.2 Hz, 1H), 5.61 (d, J=10.2 Hz, 1H), 6.06 (m, 1H), 6.88 (s, 1H), 6.94 (d, J=8.4 Hz, 1H), 7.02–7.06 (m, 2H), 7.09 (d, J=1.9 Hz, 1H), 7.13 (d, J=8.1 Hz, 1H), 7.52 (d, J=8.1 Hz, 1H), 7.82 (s, 1H), 8.26 (d, J=5.9 Hz, 1H); MS (APCI) m/z 514 (M+H)+.

Sources & evidence

ORD record: ord-589fe0ff5db34ab49c109f7928e768d2
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07129247B2

Reaction notes

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