Hydrochloric Acid → HCID 21107393, compound
Reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:19]([CH2:22][C@@H:23]2[CH2:25][O:24]2)=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2)=[O:5].[CH3:26][NH:27][CH3:28].CN1CCCC1=O.Cl>[Cl-].[Na+].O.ClCCl>[ClH:1].[Cl:1][C:2]1[CH:21]=[CH:20][C:19]([CH2:22][C@@H:23]([OH:24])[CH2:25][N:27]([CH3:28])[CH3:26])=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]12[CH2:15][CH:14]3[CH2:16][CH:10]([CH2:11][CH:12]([CH2:13]3)[CH2:17]1)[CH2:9]2)=[O:5]Participants
Procedure
2-Chloro-5-[(2R)-2-oxiranylmethyl]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide (Example 5c) (133 mg), dimethylamine (40% solution in water, 3 mL) and 1-methyl-2-pyrrolidinone (5 mL) were heated together at 80° C. in a sealed tube for 22 hours, cooled and poured into brine (50 mL), extracted into ethyl acetate (3×50 mL), washed with brine (3×50 mL), dried over anhydrous magnesium sulfate, filtered and concentrated to give an oil. This was purified by Waters' MCX resin and then by reverse phase HPLC (gradient 25–95% acetonitrile in 0.2% aqueous trifluoroacetic acid on Waters' Xterra™ column). The oil obtained was dissolved in dichloromethane (5 mL) and 1M ethereal hydrogen chloride (4 mL) was added. The mixture was concentrated to give the titled compound as a solid (41 mg).
Workup
- temperaturecooled
- extractionextracted into ethyl acetate (3×50 mL)
- washwashed with brine (3×50 mL)
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
- customto give an oil
- customThis was purified by Waters' MCX resin
- customThe oil obtained
- concentrationThe mixture was concentrated
Sources & evidence
- ORD record
- ord-ea2c6e05c6f44de683a5f62de7692115
- Source dataset
- uspto-grants-2007_06
- Patent number
- US07227038B2
Reaction notes
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