Reaction equation
[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]2Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
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.
Workup
- filtrationThe resulting solid was filtered
- washwashed with diethyl ether
Sources & evidence
- ORD record
- ord-ef1f0761c06148f982bebc0c262d5757
- Source dataset
- uspto-grants-2007_12
- Patent number
- US07307094B2
Linked notes
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