Cesium carbonate → HCID 178477281, compound

HRID 724332Notes

Reaction equation

Cl[C:2]1[N:22]=[CH:21][C:20]([F:23])=[CH:19][C:3]=1[C:4]([NH:6][C@H:7]1[CH2:12][CH2:11][C@@H:10]([NH:13][C:14](=[O:18])[CH2:15][O:16][CH3:17])[CH2:9][CH2:8]1)=[O:5].[CH2:24]([S:26][C:27]1[CH:28]=[C:29]([OH:33])[CH:30]=[CH:31][CH:32]=1)[CH3:25].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH2:24]([S:26][C:27]1[CH:28]=[C:29]([CH:30]=[CH:31][CH:32]=1)[O:33][C:2]1[N:22]=[CH:21][C:20]([F:23])=[CH:19][C:3]=1[C:4]([NH:6][C@H:7]1[CH2:12][CH2:11][C@@H:10]([NH:13][C:14](=[O:18])[CH2:15][O:16][CH3:17])[CH2:9][CH2:8]1)=[O:5])[CH3:25]

Participants

Conditions

Temperature: 55 °C

Procedure

2-Chloro-5-fluoro-N-[cis-4-(2-methoxy-acetylamino)-cyclohexyl]-nicotinamide (110 mg, 0.32 mmol), 3-ethylsulfanyl-phenol (54 mg, 0.35 mmol) and caesium carbonate (156 mg, 0.48 mmol) were suspended in dimethylformamide (2 ml) and the reaction was heated to 55° C. and stirred at this temperature under nitrogen for 18 h. The reaction was quenched with sat. ammonium chloride solution (1 ml) and water (1 ml) and the organic phase was collected by passing the mixture through a chemelute cartridge, washing with ethyl acetate (20 ml). The solvent was removed under reduced pressure and the residue was triturated with diethylether (5 ml) to give 2-(3-ethylsulfanyl-phenoxy)-5-fluoro-N-[cis-4-(2-methoxy-acetylamino)-cyclohexyl]-nicotinamide (57 mg) as an off-white solid.

Workup

customThe reaction was quenched with sat. ammonium chloride solution (1 ml) and water (1 ml)
customthe organic phase was collected
washwashing with ethyl acetate (20 ml)
customThe solvent was removed under reduced pressure
customthe residue was triturated with diethylether (5 ml)

Sources & evidence

ORD record: ord-d7b665c7e3dd44eb932dd1632f0011af
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07141586B2

Reaction notes

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