8-Methyl-8-azabicyclo[3.2.1]octan-3-amine → N-(8-Methyl-8-azabicyclo[3.2.1]oct-3-yl)-6-chloro-2-phenylbenzoxazole-4-carboxamide

HRID 506234

Reaktionsgleichung

Reaktionsgleichung von HRID 506234
[Cl:1][C:2]1[CH:3]=[C:4]2[O:8][C:7]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[N:6][C:5]2=[C:15]([C:17]([OH:19])=O)[CH:16]=1.[NH2:20][CH:21]1[CH2:27][CH:26]2[N:28]([CH3:29])[CH:23]([CH2:24][CH2:25]2)[CH2:22]1>>[CH3:29][N:28]1[CH:23]2[CH2:24][CH2:25][CH:26]1[CH2:27][CH:21]([NH:20][C:17]([C:15]1[CH:16]=[C:2]([Cl:1])[CH:3]=[C:4]3[O:8][C:7]([C:9]4[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=4)=[N:6][C:5]=13)=[O:19])[CH2:22]2

Komponenten

3

Edukt 2

HCID 4083948-Methyl-8-azabicyclo[3.2.1]octan-3-amineHCID 684576406-Chloro-2-phenyl-benzoxazole-4-carboxylic acid

Produkt 1

HCID 11509460N-(8-Methyl-8-azabicyclo[3.2.1]oct-3-yl)-6-chloro-2-phenylbenzoxazole-4-carboxamideAusbeute 20 %

Versuchsvorschrift

N-(8-Methyl-8-azabicyclo[3.2.1]oct-3-yl)-6-chloro-2-phenylbenzoxazole-4-carboxamide was prepared from 6-chloro-2-phenyl-benzoxazole-4-carboxylic acid and 3-amino-8-methyl-8-azabicyclo[3.2.1]octane using the method outlined in Step C of Example 7. This compound was obtained in 20% yield as a white solid: mp 187-190° C.; 1H NMR (500 MHz, CDCl3) δ 9.44 (d, J=7.5 Hz, 1H), 8.26 (d, J=7.1 Hz, 2H), 8.21 (d, J=2.0 Hz, 1H), 7.72 (d, J=2.0 Hz, 1H), 7.65-7.47 (m, 3H), 4.46 (q, J=7.2 Hz, 1H), 3.25 (br s, 1H), 2.38 (m, 5H), 2.26 (m, 4H), 1.84 (d, J=14.3 Hz, 2H), 2.15 (m, 1H), 2.04 (m, 1H), 1.78-1.60 (m, 3H); MS (APCI) m/z 397 [M+H]+

Aufarbeitung

  1. customThis compound was obtained in 20% yield as a white solid

Quellen und Nachweise

ORD-Eintrag
ord-f56b426541d8401889c7baa6a5eca425
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07781430B2

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