Cesium carbonate → 4-({2-[4-(5-Chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-(tetrahydro-2H-pyran-4-yl)propanoyl}amino)benzoic acid

HRID 57012Notes

Reaction equation

HRID 57012 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:39]#[N:40])=[C:6]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][N:11]([CH:16]([CH2:31][CH:32]3[CH2:37][CH2:36][O:35][CH2:34][CH2:33]3)[C:17]([NH:19][C:20]3[CH:30]=[CH:29][CH:28]=[CH:27][C:21]=3C(OCC)=O)=[O:18])[C:10](=[O:38])[CH:9]=2)[CH:7]=1.[C:41](=[O:44])([O-])[O-:42].[Cs+].[Cs+]>CO.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:39]#[N:40])=[C:6]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][N:11]([CH:16]([CH2:31][CH:32]3[CH2:37][CH2:36][O:35][CH2:34][CH2:33]3)[C:17]([NH:19][C:20]3[CH:30]=[CH:29][C:28]([C:41]([OH:42])=[O:44])=[CH:27][CH:21]=3)=[O:18])[C:10](=[O:38])[CH:9]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 10796Cesium carbonateHCID 131736948HCID 131736948, compound

Product 1

HCID 862977504-({2-[4-(5-Chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-(tetrahydro-2H-pyran-4-yl)propanoyl}amino)benzoic acid

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

1.07 g (1.89 mmol) of ethyl ({2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-(tetrahydro-2H-pyran-4-yl)propanoyl}amino)benzoate (racemate) in 24 ml of methanol/water (4/1) were reacted with 1.24 g (3.79 mmol) of caesium carbonate according to General Method 4. Yield: 1.24 g (purity 73%, 88% of theory)

Sources & evidence

ORD record
ord-ba86e05707994628bfb4952cc01e61a8
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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