4-Hydroxypyrrolidine → HCID 21906805, compound

HRID 1005834Notes

Reaction equation

HRID 1005834 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[CH2:43][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][CH2:43][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

4

Reactant 3

HCID 982104-HydroxypyrrolidineHCID 4186202N-AcetylhomopiperazineHCID 865858674-(4-(2,3-Dihydro-benzo(1,4)dioxin-6-ylsulfanyl)-3-trifluoromethyl-phenyl)-pyridine

Product 1

HCID 21906805HCID 21906805, 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 N-acetylhomopiperazine. A yellow solid 133 was obtained (0.021 g, 40%). 1H-NMR (CDCl3, 400 MHz) δ 2.01-2.10 (m, 2H), 2.08 (s, 3H), 3.52-3.60 (m, 2H), 3.76-3.91 (m, 4H), 4.01-4.06 (m, 1H), 4.11-4.16 (m, 1H), 4.28-4.34 (m, 4H), 6.85 (s, 1/3H), 6.87 (s, 2/3H), 6.95 (d, J=8.4 Hz, 1H), 6.97 (d, J=6.6 Hz, 1H), 7.05 (dd, J=1.4 Hz, 8.4 Hz, 1H), 7.10 (d, J=2.2 Hz, 1H), 7.11-7.14 (m, 1H), 7.50-7.56 (m, 1H), 7.81 (s, 1/3H), 7.82 (s, 2/3H), 8.26-8.30 (m, 1H);MS (APCI) m/z 530 (M+H)+.

Sources & evidence

ORD record
ord-b1abcec0d036464e896def95911d8bd2
Source dataset
uspto-grants-2004_09
Patent number
US06787542B2

Reaction notes

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