Potassium Carbonate → 1-[4-Cyano-2-(propane-1-sulfonyl)-benzyl]-6-methyl-4-oxo-5-(3-trifluoromethyl-phenyl)-1,4-dihydro-pyridine-3-carboxylic acid methylamide

HRID 512514Notes

Reaction equation

[CH3:1][NH:2][C:3]([C:5]1[C:10](=[O:11])[C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)=[C:8]([CH3:22])[N:7]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][C:25]=2Br)[CH:6]=1)=[O:4].[CH2:33]([S:36]([O-:38])=[O:37])[CH2:34][CH3:35].[Na+].N1CCC[C@H]1C(O)=O.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.[Cu]I>[CH3:1][NH:2][C:3]([C:5]1[C:10](=[O:11])[C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)=[C:8]([CH3:22])[N:7]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][C:25]=2[S:36]([CH2:33][CH2:34][CH3:35])(=[O:38])=[O:37])[CH:6]=1)=[O:4]

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of preparation 25a (70 mg, 139 μmol), sodium 1-propylsulfinate (54 mg, 415 μmol), L-proline (20 mg, 174 μmol), CuI (7 mg, 37 μmol), K2CO3 (24 mg, 174 μmol) in DMSO (0.7 mL) is heated 60 min at 110° C. The reaction mixture is purified by preparative reversed-phase HPLC (XBridge, gradient of methanol in water, 0.3% NH4OH, 60° C.). Yield: 11 mg (15% of theory); ESI mass spectrum: [M+H]+=532; Retention time HPLC: 1.06 min (Z003—001).

Workup

customThe reaction mixture is purified by preparative reversed-phase HPLC (XBridge, gradient of methanol in water, 0.3% NH4OH, 60° C.)
custom1.06 min (Z003—001)

Sources & evidence

ORD record: ord-92cbf3b37c1f47b6830f4878d6dca008
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09102624B2

Reaction notes

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