Iodoethane → 1-Ethyl-6-methyl-4-oxo-5-(3-trifluoromethyl-phenyl)-1,4-dihydro-pyridine-3-carboxylic acid 4-methanesulfonyl-benzylamide

HRID 524342Notes

Reaction equation

[CH3:1][S:2]([C:5]1[CH:32]=[CH:31][C:8]([CH2:9][NH:10][C:11]([C:13]2[C:18](=[O:19])[C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=3)=[C:16]([CH3:30])[NH:15][CH:14]=2)=[O:12])=[CH:7][CH:6]=1)(=[O:4])=[O:3].C([O-])([O-])=O.[K+].[K+].I[CH2:40][CH3:41]>CN(C=O)C.CO>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][NH:10][C:11]([C:13]2[C:18](=[O:19])[C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:28])([F:27])[F:29])[CH:21]=3)=[C:16]([CH3:30])[N:15]([CH2:40][CH3:41])[CH:14]=2)=[O:12])=[CH:31][CH:32]=1)(=[O:4])=[O:3]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 6-methyl-4-oxo-5-(3-trifluoromethyl-phenyl)-1,4-dihydro-pyridine-3-carboxylic acid 4-methanesulfonyl-benzylamide (preparation 1, 100 mg, 0.215 mmol), K2CO3 (48 mg, 0.344 mmol) and iodoethane (20 μL, 0.250 mmol) in DMF (1 mL) is stirred for 30 min at 80° C. (microwave). The reaction mixture is diluted with MeOH, filtered and purified by preparative reversed-phase HPLC (XBridge, gradient of methanol in water, 0.3% NH4OH, 60° C.). Yield: 52 mg (49% of theory); ESI mass spectrum: [M+H]+=493; Retention time HPLC: 1.03 min (Z003_001).

Workup

filtrationfiltered
custompurified by preparative reversed-phase HPLC (XBridge, gradient of methanol in water, 0.3% NH4OH, 60° C.)
custom1.03 min (Z003_001)

Sources & evidence

ORD record: ord-5c0decab837f4e628f7f90cbc0aa665d
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09340507B2

Reaction notes

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