Hydrochloric Acid → HCID 131721761, compound
Reaction equation
[ClH:1].[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[C:10](=[O:14])[CH:9]([CH2:15][N:16]1[CH2:21][CH2:20][CH:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:18][CH2:17]1)[CH2:8][CH2:7]2.CI.[CH3:30]CN(CC)CC.Cl>C1COCC1>[ClH:1].[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[C:10](=[O:14])[C:9]([CH3:30])([CH2:15][N:16]1[CH2:21][CH2:20][CH:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:18][CH2:17]1)[CH2:8][CH2:7]2Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a solution of the title compound of Example 1 (379 mg, 1.084 mmol, free base) in THF (10 mL) at -78° C. under nitrogen with stirring was added a solution of KN(SiMe3)2 (0.5 M in toluene, 2.39 mL, 1.19 mmol). The reaction mixture was stirred at -78° C. for 5 minutes followed by the addition of methyl iodide (0.223 mL, 3.58 mmol). The mixture was stirred at -78° C. for another 15 minutes, then kept at -16° C. for 0.5 hours followed by the addition of Et3N (0.832 mL, 5.96 mmol). The mixture was quenched with saturated sodium bicarbonate and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and concentrated to afford a thick gummy residue. This was converted to its hydrochloride by treatment with hydrochloric to afford the title compound as a white solid, mp 185-186° C.
Workup
- stirringThe mixture was stirred at -78° C. for another 15 minutes
- waitkept at -16° C. for 0.5 hours
- customThe mixture was quenched with saturated sodium bicarbonate
- extractionextracted with ethyl acetate
- washThe organic layer was washed with brine
- dry with materialdried over magnesium sulfate
- concentrationconcentrated
- customto afford a thick gummy residue
Sources & evidence
- ORD record
- ord-41ff402e3a4b48c58c6a4c6b57ab1672
- Source dataset
- uspto-grants-2000_04
- Patent number
- US06048877
Reaction notes
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