2-Methoxyethylamine → HCID 131733419, compound
Reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH2:5].[C:6]([O:10][C:11](=[O:33])[NH:12][C@@H:13]1[CH2:18][CH2:17][CH2:16][N:15]([C:19](=[O:32])[C:20]2[CH:25]=[C:24]([N+:26]([O-:28])=[O:27])[C:23](Cl)=[C:22]([O:30][CH3:31])[CH:21]=2)[CH2:14]1)([CH3:9])([CH3:8])[CH3:7]>CN(C)C=O>[C:6]([O:10][C:11](=[O:33])[NH:12][C@@H:13]1[CH2:18][CH2:17][CH2:16][N:15]([C:19](=[O:32])[C:20]2[CH:25]=[C:24]([N+:26]([O-:28])=[O:27])[C:23]([NH:5][CH2:4][CH2:3][O:2][CH3:1])=[C:22]([O:30][CH3:31])[CH:21]=2)[CH2:14]1)([CH3:9])([CH3:7])[CH3:8]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
2-Methoxyethylamine (0.15 mL, 1.741 mmol) was added to a stirred solution of (R)-tert-butyl(1-(4-chloro-3-methoxy-5-nitrobenzoyl)piperidin-3-yl)carbamate (280 mg, 0.406 mmol) in N,N-dimethylformamide (DMF) (1.5 mL) at rt under nitrogen. The reaction mixture was heated to 80° C. and stirred under nitrogen overnight (16 h). LC/MS showed that the desired product had formed with 55% purity. Water (75 mL) and diethyl ether (75 mL) were added to the reaction mixture and the layers separated. The aqueous layer was further extracted with diethyl ether (2×50 mL). The organic layers were collected, dried (Na2SO4), passed through a hydrophobic frit and concentrated under vacuum to afford 330 mg of crude product as an orange oil. The crude product was dissolved in a minimum volume of DCM and purified by column chromatography (25 g silica). The column was eluted with a gradient of 60-100% ethyl acetate/cyclohexane. TLC was used to determine product fractions and the appropriate fractions were collected and concentrated under vacuum to afford—(R)-tert-butyl(1-(3-methoxy-4-((2-methoxyethyl)amino)-5-nitrobenzoyl)piperidin-3-yl)carbamate (165.7 mg, 0.366 mmol, 90% yield)
Sources & evidence
- ORD record
- ord-e104a39a248148e1aef62d95b5ef25ae
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09127003B2
Reaction notes
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