Quinuclidine, 3-amino-, dihydrochloride → N-(1-Azabicyclo[2.2.2]oct-3-yl)-5-chloro-2-phenylbenzoxazole-7-carboxamide

HRID 969842

Reaktionsgleichung

Reaktionsgleichung von HRID 969842
[Cl:1][C:2]1[CH:3]=[C:4]([C:17]([OH:19])=O)[C:5]2[O:9][C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[N:7][C:6]=2[CH:16]=1.Cl.Cl.[NH2:22][CH:23]1[CH:28]2[CH2:29][CH2:30][N:25]([CH2:26][CH2:27]2)[CH2:24]1>>[N:25]12[CH2:30][CH2:29][CH:28]([CH2:27][CH2:26]1)[CH:23]([NH:22][C:17]([C:4]1[C:5]3[O:9][C:8]([C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=4)=[N:7][C:6]=3[CH:16]=[C:2]([Cl:1])[CH:3]=1)=[O:19])[CH2:24]2

Komponenten

3

Edukt 2

HCID 197853Quinuclidine, 3-amino-, dihydrochlorideHCID 684565005-Chloro-2-phenylbenzoxazole-7-carboxylic acid

Produkt 1

HCID 11646621N-(1-Azabicyclo[2.2.2]oct-3-yl)-5-chloro-2-phenylbenzoxazole-7-carboxamideAusbeute 56 %

Versuchsvorschrift

N-(1-Azabicyclo[2.2.2]oct-3-yl)-5-chloro-2-phenylbenzoxazole-7-carboxamide was prepared from 5-chloro-2-phenyl-benzoxazole-7-carboxylic acid and 3-aminoquinuclidine dihydrochloride using the method outlined in Step C of Example 7. This compound was obtained in 56% yield as a white solid: mp 283-285° C.; 1H NMR (300 MHz, CH3OD) δ 8.22 (dd, J=8.1, 1.5 Hz, 2H), 7.86 (d, J=2.1 Hz, 1H), 7.70 (d, J=2.1 Hz, 1H), 7.64-7.56 (m, 3H), 4.27-4.24 (m, 1H), 3.50-3.42 (m, 1H), 3.12-2.86 (m, 5H), 2.17 (q, J=3.0 Hz, 1H), 2.11-2.06 (m, 1H), 1.85-1.73 (m, 2H), 1.74-1.67 (m, 1H); MS (ESI) m/z 382[M+H]+.

Aufarbeitung

  1. customThis compound was obtained in 56% yield as a white solid

Quellen und Nachweise

ORD-Eintrag
ord-4ceda8a2d89a4167afa66237847045a0
Quelldatensatz
uspto-grants-2007_12
Patentnummer
US07307094B2

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