1-(3-Hydroxypropyl)pyrrolidin-2-one → 3-Fluoro-N-{4-[3-(2-oxopyrrolidin-1-yl)propoxy]-1-naphthyl}-5-piperidin-1-ylbenzamide

HRID 1171362

Reaktionsgleichung

Reaktionsgleichung von HRID 1171362
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([NH:12][C:13](=[O:19])OC(C)(C)C)=[CH:4][CH:3]=1.[F:20][C:21]1[CH:22]=[C:23]([CH:27]=[C:28]([N:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)[CH:29]=1)C(O)=O.O[CH2:37][CH2:38][CH2:39][N:40]1[CH2:44][CH2:43][CH2:42][C:41]1=[O:45]>>[F:20][C:21]1[CH:22]=[C:23]([CH:27]=[C:28]([N:30]2[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]2)[CH:29]=1)[C:13]([NH:12][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([O:1][CH2:37][CH2:38][CH2:39][N:40]2[CH2:44][CH2:43][CH2:42][C:41]2=[O:45])=[CH:3][CH:4]=1)=[O:19]

Komponenten

4

Edukt 3

HCID 5667441-(3-Hydroxypropyl)pyrrolidin-2-oneHCID 10923237tert-Butyl (4-hydroxynaphthalen-1-yl)carbamateHCID 595531803-Fluoro-5-piperidinylbenzoic acid

Produkt 1

HCID 595531013-Fluoro-N-{4-[3-(2-oxopyrrolidin-1-yl)propoxy]-1-naphthyl}-5-piperidin-1-ylbenzamide

Versuchsvorschrift

Compound is prepared from tert-butyl (4-hydroxy-1-naphthyl)carbamate, 3-fluoro-5-piperidin-1-yl-benzoic acid and 1-(3-hydroxy-propyl)-pyrrolidin-2-one according to conditions described in general procedure D. A pink solid is produced (42 mg). Mp: 88-89° C.; 1H NMR (300 MHz, CDCl3) δ 1.69 (s, 6H), 1.95-2.04 (m, 2H), 2.10-2.18 (m, 2H), 2.34-2.39 (m, 2H), 3.26 (s, 4H), 3.37-3.45 (m, 2H), 3.50-3.55 (m, 2H), 4.09-4.13 (m, 2H), 6.72-6.77 (m, 2H), 7.03 (d, J=8.4 Hz, 1H), 7.33 (s, 1H), 7.46-7.55 (m, 2H), 7.63 (d, J=7.8 Hz, 1H), 7.82 (d, J=7.5 Hz, 1H), 8.23 (s, 1H), 8.27-8.30 (m, 1H); MS 490 (M+1).

Aufarbeitung

  1. customA pink solid is produced (42 mg)

Quellen und Nachweise

ORD-Eintrag
ord-df59f39f1bb3445e844ebde3e1e6907f
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07829560B2

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