Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | HCID 68999163 | HCID 68999163 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Product | HCID 69001040 | HCID 69001040 | 78% |
Reaction Steps
To a solution of (S)—N-(1-azabicyclo[2.2.2]oct-3-yl)-2-benzylbenzoxazole-4-carboxamide (84 mg, 0.23 mmol) in methanol (1.5 mL) was added a solution of HCl in diethyl ether (1 N, 0.5 mL, 0.5 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 (S)—N-(1-azabicyclo[2.2.2]oct-3-yl)-2-benzylbenzoxazole-4-carboxamide hydrochloride (71 mg, 78%) as a white solid: 1H NMR (500 MHz, DMSO-d6) δ 10.05 (br s, 1H), 9.19 (d, J=7.1 Hz, 1H), 7.95 (d, J=8.0 Hz, 1H), 7.88 (d, J=8.0 Hz, 1H), 7.52 (t, J=7.9 Hz, 1H), 7.45-7.30 (m, 5H), 4.48 (s, 2H), 4.37-4.32 (m, 1H), 3.75-3.65 (m, 1H), 3.22-3.15 (m, 3H), 3.10-3.05 (m, 2H), 2.15-2.10 (m, 1H), 1.95-1.90 (m, 2H), 1.80-1.60 (m, 2H); MS (ESI+) m/z 362 (M+H); HPLC>99% (AUC), tR=11.81 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07553846B2 |
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| Source dataset | uspto-grants-2009_06 |
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| ORD ID | ord-068877c922fa4cb6ac6220e2f324970d |
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| Source note | uspto-grants-2009_06 |
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