Reaktionsgleichung
[CH3:1][N:2]1[CH:7]2[CH2:8][CH2:9][CH2:10][CH:3]1[CH2:4][CH:5]([NH:11][C:12]([C:14]1[CH:15]=[CH:16][CH:17]=[C:18]3[O:22][C:21]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[OH:29])=[N:20][C:19]=13)=[O:13])[CH2:6]2.[ClH:30]>CO.C(OCC)C>[ClH:30].[CH3:1][N:2]1[CH:3]2[CH2:10][CH2:9][CH2:8][CH:7]1[CH2:6][CH:5]([NH:11][C:12]([C:14]1[CH:15]=[CH:16][CH:17]=[C:18]3[O:22][C:21]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[OH:29])=[N:20][C:19]=13)=[O:13])[CH2:4]2Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
To a solution of N-(9-methyl-9-azabicyclo[3.3.1]non-3-yl)-2-(2-hydroxyphenyl)benzoxazole-4-carboxamide (66 mg, 0.17 mmol) in methanol (1.0 mL) was added a solution of HCl in diethyl ether (1 N, 0.18 mL, 0.18 mmol) at room temperature slowly. The reaction mixture was diluted with diethyl ether. The resulting solid was filtered and washed with diethyl ether to afford N-(9-methyl-9-azabicyclo[3.3.1]non-3-yl)-2-(2-hydroxyphenyl)benzoxazole-4-carboxamide hydrochloride (39 mg, 54%) as a white solid: 1H NMR (500 MHz, CDCl3) δ 12.30 (br s, 0.5H), 12.01 (br s, 0.5H), 8.30-8.10 (m, 2H), 7.90-7.75 (m, 1H), 7.58-7.50 (m, 2H), 7.18-7.12 (m, 2H), 4.95-4.85 (m, 0.5H), 4.70-4.60 (m, 0.5H), 3.70-3.55 (m, 2H), 3.25-3.15 (m, 1H), 3.00-2.75 (m, 5H), 2.50-2.00 (m, 5H), 1.90-1.50 (m, 4H); MS (ESI+) m/z 392 (M+H); HPLC 96.7% (AUC), tR=12.44 min.
Aufarbeitung
- filtrationThe resulting solid was filtered
- washwashed with diethyl ether
Quellen und Nachweise
- ORD-Eintrag
- ord-ea4de87a79684b1f9872b2404ed4df46
- Quelldatensatz
- uspto-grants-2010_08
- Patentnummer
- US07781430B2
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