Triethylamine → HCID 44469673, Verbindung

HRID 1878820Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1878820
[C:1]([C:3]1[CH:27]=[CH:26][C:6]([CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([NH:14][C:15]([C:17]3[CH:25]=[CH:24][C:20]([C:21]([OH:23])=O)=[CH:19][CH:18]=3)=[O:16])[CH2:10][CH2:9]2)=[CH:5][CH:4]=1)#[N:2].C(N(CC)CC)C.CN(C(ON1N=N[C:45]2[CH:46]=[CH:47][CH:48]=[N:49][C:44]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:59]([O:61][C:62]1[CH:74]=[CH:73][C:65]([CH2:66]C2CCNCC2)=[CH:64][CH:63]=1)[CH3:60]>CN(C)C=O.O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:16])[C:17]3[CH:18]=[CH:19][C:20]([C:21]([CH:46]4[CH2:45][CH2:44][N:49]([CH2:66][C:65]5[CH:73]=[CH:74][C:62]([O:61][CH2:59][CH3:60])=[CH:63][CH:64]=5)[CH2:48][CH2:47]4)=[O:23])=[CH:24][CH:25]=3)[CH2:10][CH2:9]2)=[CH:26][CH:27]=1)#[N:2]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 47782654-(4-ethoxybenzyl)piperidineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 69008872HCID 69008872, Verbindung

Produkt 1

HCID 44469673HCID 44469673, VerbindungAusbeute 450,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred mixture of 4-(1-(4-cyanobenzyl)piperidin-4-ylcarbamoyl)benzoic acid (100 mg, 0.275 mmol) in anhydrous N,N-dimethylformamide (3 mL) was added triethylamine (84 μl, 0.825 mmol), HATU (115 mg, 0.3 mmol), and 4-(4-ethoxybenzyl)piperidine (61 mg, 0.275 mmol). The mixture was stirred at room temperature overnight and then poured into water. The resulting solids were collected by filtration, purified by column chromatography to yield 0.7 g (55%) of N-(1-(4-cyanobenzyl)piperidin-4-yl)-4-(1-(4-ethoxybenzyl)piperidine-4-carbonyl)benzamide (compound 27) as an offwhite solid. 1H-NMR (CDCl3, 300 MHz): δ 7.761 (d, 2H), 7.600 (m, 2H), 7.434 (m, 4H), 7.022 (d, 2H), 6.812 (d, 2H), 6.022 (d, 1H), 4.658 (m, 1H), 3.994 (dd, 2H), 3.569 (m, 3H), 2.885 (m, 4H), 2.505 (m, 2H), 2.227 (m, 2H), 2.049 (m, 2H), 1.639 (m, 6H), 1.405 (m, 3H); LCMS (m/z): 565 (MH+).

Aufarbeitung

  1. filtrationThe resulting solids were collected by filtration
  2. custompurified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-7398dc98a7e647058993d97dffedcb13
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08314107B2

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